Lesbian overthinks her gender expression. News at 11.
August 2, 2012 5:47 AM   Subscribe

I'm a 22-year-old lesbian. I have never made any effort to look hot, but suddenly I want to, and it's raising some serious identity issues for me.

Hygiene/beauty-wise, all I do is shower daily, brush my teeth, comb my hair (though it tends to go every which-way), and wear deodorant, clean clothes (some men's, some women's), and moisturizer (for the SPF). I don't own any makeup and I don't know how to apply it. Basically, I look like I don't give a fuck.

Here's the thing, though—I do give a fuck, and I think my apparent apathy's a holdover from a time when I truly wasn't comfortable with myself. As a closeted teen/pre-teen, I wore dingy sweats everyday and kept a copy of The Beauty Myth in my junior high school locker. (I'm sure NO ONE ever suspected.) I defined myself in opposition to other girls because I felt like I could never truly be one of them anyway and was too proud to try. I also did it to distance myself from them so I didn't have to deal with my attraction. On a less psychosexual level, I felt like if I tried to look pretty, people would see right through it and laugh at me.

I had a boyfriend in high school and a couple more in college, along with some random male hookups (I came out "bisexual" at 18). Almost every single first makeout session would include a moment where the guy would look at me real close and then quizzically remark, "You know, you're really pretty," like he'd never noticed before and was pleasantly surprised. Secretly, I loved hearing that—in my mind, it indicated that I wasn't naturally uglier than other girls, but merely had less superficial values. (Ugh.)

Now I've graduated college and am finally out as gay, not bi. My frumpiness is no longer really a source of political pride for me anymore, because I've internalized patriarchal beauty standards enough to only be attracted to women who mostly fit them (yeah, stone me). I'm not trying to imply that a butch or androgynous woman who likes feminine women is necessarily a hypocrite; just that my former feminister-than-thou attitude about not meeting those standards no longer makes sense. Also, it's not like I'm some Jackie Warner/Kate Moennig type—I just look like a troll.

I don't know what sort of gender presentation I'd have if I didn't go through such a long phase of self-loathing, but I suspect that the answer is still not "Barbie". The last time I really dressed up girly was a couple years ago and I felt like I was in drag, but hey, I don't feel terribly comfortable with the way I look now either. Ultimately, I'd like to look like a cute urban 20-something queer girl that other cute urban 20-something queer girls could see themselves dating, instead of an overgrown 3rd grader with blotchy skin and gigantic boobs.

I suppose I know, in broad strokes, how to go about changing my image: learn how to tame my hair, get some makeup and try to even my skin tone a little on nights that I go out, buy trendy-looking clothes I normally wouldn't look at twice, get less-dorky glasses the next time I need a new prescription. If you have any practical advice on those matters, it's more than welcome. (I'm 5'5", 140 lbs, white, and would look ridiculous with hair any shorter than chin-length.) But I guess my real question is, though, how do I not feel so ridiculous trying? I spent my entire adolescence acting either aggressively opposed to this sort of stuff or innocently too "deep" for it. It's a big part of who I was, which is probably why it feels like such a big deal changing it. I don't have any real reason to believe I won't just feel like a potential poser again. Also, I feel like most other people have settled into their style by this age even if do they switch things up here and there, so this sort of deliberate change feels kind of life-stage inappropriate.

As for what I can afford... I make $35,000 a year, my rent's $650/month, and I'm not in any debt. Obviously cheaper is better, but I'm willing to throw a little bit of money at this problem.

(Also, yes, I know that confidence is my biggest issue and that that's not primarily a matter of looks, but I wanted this question to be targeted.)

Throwaway email: anon724 at gmail
posted by anonymous to Human Relations (63 answers total) 59 users marked this as a favorite
Oh my goodness, I've got a bit of a girl crush on you. You write so beautifully.

My advice is to go slowly at this... I don't identify as queer, but had many of the same issues as yourself at the same age. I found that starting to wear fitted clothes, in flattering styles.... still trousers and flat shoes and stuff.... but slimming it down, getting a bit of colour involved... maybe a funky statement necklace... and I looked around at the kind of chicks that I thought looked cool, and stole ideas from them.

But it took me while to find my style, then I got old and fat and tired and broke and it all changed again.

But I started with the slimmer look and worked from there. I also spent a bit of time getting advice on my hair from a hairdresser. That also changed for me... but it was a good start in getting my confidence.

The very best of luck to you, I hope one of my daughters meets someone as lovely as you one day.

Also... I'm very happy to email any motherly advice you're interested in, if you'd like. I"m not really THAT old. Although my three year old thinks so.
posted by taff at 5:56 AM on August 2, 2012 [9 favorites]

But I guess my real question is, though, how do I not feel so ridiculous trying? I spent my entire adolescence acting either aggressively opposed to this sort of stuff or innocently too "deep" for it. It's a big part of who I was, which is probably why it feels like such a big deal changing it. I don't have any real reason to believe I won't just feel like a potential poser again.

Then that's how you regulate what you change.

You're actually wrong about "most people settling into their 'look'" by a certain age -- people are constantly changing their whole lives, on the inside, and sometimes that change on the inside makes them feel that their outside doesn't really "match" the new inside any more. You may be feeling awkward especially because you were trying to put on a different outward identity like it was a costume, and this is just the first time you've put thought into "but does it match 'me'?" That's VERY much a part of what your 20's are about - you've been trying on these different roles like costumes, both appearance-wise AND personality-wise, but your 20's are about fine-tuning that. So what you're going through is totally, totally normal.

Just try stuff. Put aside everything you've heard or you believe about "girly girls are like this while feminists and womyn are like that", and focus on "what do I personally as a unique individual want to do." Then try stuff. Try little stuff, and if you like it, then great. If you try makeup and you look at it and think "holy shit that makes my eyes look gorgeous," then great, go ahead and do it. If you try it and think "what the hell, I have stuff on my face and that looks weird," then don't do it. Same with clothes, or hair, or anything.

You are allowed to change your look as many times as you want. You are constantly changing, and appearance is a very personal expression of the inner self. As you get to know your inner self better, and as that inner self changes, your outward look also deserves to change as well.
posted by EmpressCallipygos at 5:59 AM on August 2, 2012 [25 favorites]

TLDR but with any remodeling of an identity you probably should start with some role-model. As usual, looks help to define identity so look for a role-model who you feel meets some of your qualities and start picture shopping via Google or whatever-mag-you-see. It probably doesn't hurt to hit up the couture fashion mags to see if you are inspired.

Use the role-model as a stepping-off point and not a permanent idea of "what is she wearing this week". Because obviously the first try may not work and you'll have to modify it later on.
posted by JJ86 at 6:04 AM on August 2, 2012

Ok, I've just come back with another VITAL suggestion. Your eyebrows. I'm not sure where you are, but there will be someone, somewhere in your town that knows the very, very best eyebrow stylist available. Get them shaped professionally once. Just once is all it takes, and then you maintain with a good pair of your own tweezers.

Don't go to a salon and just get the chick that does, nails, legs, eyelashes and fake tans. You need an eyebrow specialist. And you need to ask around as to who that is. (Next week's ask metafilter question?)

Trust me, this one small step will dramatically and cheaply make you feel wonderful. Seriously, if I could take aside all young, blossoming women and impart this one piece of advice when they're feeling less than stellar, it would be all about the eyebrows.

One day you'll email me and say, "Taff, you were sooooooooo right!" You will. And then you'll tell all your friends and the good word will be passed on!

(I'm assuming you're American based on the way you wrote your weight...

Here is where Sydney lasses go. Just as an idea. Warning, the website is HORRENDOUS!!!)

Much more luck, I'm in your corner possum.
posted by taff at 6:05 AM on August 2, 2012 [21 favorites]

Also, I feel like most other people have settled into their style by this age even if do they switch things up here and there, so this sort of deliberate change feels kind of life-stage inappropriate.

By 22? I don't think so, these days, and I don't think this is life-stage inappropriate at all. I don't think it's uncommon at all for people's style to change when they leave college and start working full-time.

But I guess my real question is, though, how do I not feel so ridiculous trying?

I'm a guy so take my advice with a grain of salt, but I think the way not to feel like you are in costume is to change one thing at a time, trying out alternatives until you feel like you've gotten it right and you feel comfortable with it, and only then moving on to another component of your appearance.
posted by enn at 6:10 AM on August 2, 2012 [3 favorites]

Agree wtih Taff on the eyebrows. Coiffed eyebrows can make someone look absolutely beautiful with no makeup. I have a huge difference in appearance once I get them shapped (they're very 1950's pinup-arched and many people always comment on how beautiful they are and enhance my eyes).

For makeup, while I love how Kim Kardashian looks, on me, I would look like a messed up whore. So I would suggest get a good concealer, mascara, and faint lipstick (lately I'm wearing Burt's Bees lip shimmer; provides a touch of color without the pain in the assness of lipstick).

While I wear eyeshadow and eyeliner, mascara alone does make the eyes pop.
posted by stormpooper at 6:15 AM on August 2, 2012

Like enn and taff have alluded to, small bits can make a big difference! For example, eyeliner on the top of the eyelids brings attention to your eyes, and help give some focus to your face. I have small-ish eyes, and a thin line of brown/ black eyeliner makes all the difference.

The best part of building a look is that it *can be changed*, so if you don't like it? No big, just swap it out!

Best of luck. :)
posted by lineofsight at 6:16 AM on August 2, 2012

As a 20-something queer girl who presents more on the masculine side of the spectrum, I can totally understand where you're coming from. Although I've been comfortable about my appearance for awhile, it was always tough to find the type of clothes that reflected my own confidence.

Have you tried reading the fashion columns over on Autostraddle? I think these articles could be a great source of information for you just because they cover such a wide variety of fashion trends within queer culture. They often feature more of a middle ground between the butch/femme binary, so there's a lot to draw from.

Additionally, you might be interested in creating an account with Polyvore. This website operates a little like a fashion version of Pinterest, where you can create a collage of the different styles you like and then work to figure out what kind of definitive look you may want to present. Also, Polyvore does this great thing where you can ask a question, something like "Where can I find this men's jacket, but in sizes for women?" and then the whole community will reply with tips and websites that might be helpful.

Good luck!
posted by _superconductor at 6:18 AM on August 2, 2012 [6 favorites]

Yeah, start slow. Buy a girly blouse at a thrift store and wear it around your house. Do you like it? Buy another one. Buy a skirt -- nothing dramatic -- knee-length, A-line. Try it out for a while. If you don't like it, don't force it.

Very much agree about the eyebrows. Other small things that can make a big difference in terms of appearance: mascara, tinted lip gloss (I like this stuff). If you have pierced ears, or would consider getting them pierced, big dangly earrings are very feminine.

Don't worry too much about being a "late bloomer." I spent most of my early twenties experimenting with my image (bright yellow tights under rolled-up jeans with rainbow-striped socks? why not!) and you are still very much in the window where redefining yourself is not just acceptable but expected.

Good luck!
posted by baby beluga at 6:18 AM on August 2, 2012

You should read some queer femme tumblrs! I am a butch queer person of indeterminate gender who isn't really attracted to femme women and reading a lot of those totally changed my feelings about bodies and femme presentation.

Sadly, I can't link to any because I'm at work and most of them are titled, like, "fuck yeah [thing] queer femmes"...but you might try googling "a l'allure garconniere tumblr" for starters. She reposts a lot of stuff.

Now, I'd also suggest looking at some cool political queer femme ones - I read one that goes by the attractive name of "puking fancy" and one called "tangled up in lace" and a bunch that they repost from - those connect a lot of stuff about race and class with gender presentation in ways that I find helpful.

Also try reading some about fat femme women - I've found that my body norms have shifted a lot simply because I now see a lot of images of fat femme women being all fashion-y. You can, of course, date whoever you please - but if you can hack that "patriarchal beauty norms" thing, your dating pool is suddenly much deeper, so to speak - since you can date, like, the fat chicks too.

I cannot overemphasize the difference that reading a lot of tumblrs over the course of five or six months made to me. And it was totally free.

Also, people reblog beauty stuff all the time.

In terms of changing your style at the advanced age of early-twenties....ok, my parents gave me this series of messages about how I was "too old" for things starting when I was about ten...Too old for Halloween, too old for that book or that job or that hairstyle or getting a graduate degree (I was "too old" for a graduate degree at 24, to give you some idea) too old to change jobs...and that has really stayed with me. I've missed a lot of things because I told myself I was too old. Now, your experience when you're older is different than when you're younger, and some things just don't work - but never, ever shut yourself out of trying something because you are "too old" unless there is a clear-cut physical or economic reason - you're "too old" to take up mountain-climbing at 65, you're probably too old to date an 18-year-old once you start really looking middle-aged, etc.

I changed my style dramatically in my mid-thirties. How about that? I went from a premature artsy-older-lady look (lots of volume, dark colors, flow, big skirts, unusual shirts, asymmetry, drama) to a sort of preppy queer look inspired very much by weird gay or queerish intellectuals and writers of the past...By which I mean I dress a bit like Gore Vidal crossed with radical gay sixties dudes. And I am a lot happier. I no longer worry about my "look" because my clothes reflect my character, are comfortable, etc. I have shirts from four years ago that I still wear, whereas before there was a lot of churn in my wardrobe because I never really liked anything.

And I do owe it to the internet - not all to tumblr, as this started before tumblr was a thing, but definitely to queer blogs (and men's style blogs, yeah, but that doesn't really apply in your case.)

I'm not trying to imply that a butch or androgynous woman who likes feminine women is necessarily a hypocrite

This, though - please work on that 'necessarily'. I think I get where you're coming from - I was really hung up on anxiety about being attracted to people 'out of my league' because I felt so hideously troll-like and felt like a hypocrite because how could I be attracted to them when I myself wasn't good-looking? I also projected a lot of shit onto other people. So, like, as a butch person, I hope you aren't projecting "hypocrisy" onto me and my ilk. Our style and gender expression is often just as studied as yours, for one thing.

On another note: I think femme-ness is having a cultural moment in queer communities. And like everything that has a cultural moment, that's both because there are unmet needs around femme stuff and because it's easy to recuperate into capitalism and patriarchy. (Everything has two sides.) So when you're thinking about fancier/femme gender presentation, I don't know, be thoughtful about how femme works in the broader culture, how it is defined in queer culture, etc etc.
posted by Frowner at 6:19 AM on August 2, 2012 [29 favorites]

You are so awesome.

I have no idea what style I am yet and I am beyond middle age now. I was never a girly girl and a lot of times, it feels like I am pretending to be something I am not. Like when I was the maid of honor for my aunt's wedding and when I was dressed up for high school graduation. I was always an Izod and Levi jeans with Adidas sneakers girl. In high school, I attempted to be girlier but that just meant I wore purple sweats with a sparkly design on it once in a while. When I got to college, I cut my hair really short. My guy friend asked me why the hell I did that. He said, "you look like a guy with boobs." I'm going to mail you because I want write so much more. So, while I was growing it back out, I was doing the sweater, jeans, penny loafers thing. I wore a lot of army stuff. Camo. My dad was in the army so I had a lot of stuff to go through. Now, I wear dresses. It's easy because I am busy and it's great when it rains because I just have to dry my legs instead of find a way to dry my pant legs.

Anyway, to make a short story long, you have to think about what is comfortable first. Once you are comfortable, you won't feel like you are in drag or something. Make up is easy. Use a tinted moisturizer with SPF and use a tinted lip balm. You don't have to look like someone else to look presentable, just define your lips and if you are really going nuts, mascara.

I am going to mail you because I want to write more.
posted by Yellow at 6:19 AM on August 2, 2012

But I guess my real question is, though, how do I not feel so ridiculous trying?

IMO this is normal and a good thing. You're wanting to make a major changes, major changes are by definition outside of your comfort zone. You'll probably feel that way for a while.

And since you want to make these changes for you, well, by definition you're not a poser.
posted by anti social order at 6:21 AM on August 2, 2012

I recommend taking some time to play.

If the first time you try out a new look you really want it to be flattering and awesome, and you want yourself to be perfectly comfortable with it immediately, well, that's a lot of expectations to be placing on an outfit.

If you just set aside some time to go around shops and play dress-up, it's a lot more low-stakes. You can try on a silly frock just for the fun of it, without having to confront all of your personal frock demons at once. You can look like a cowboy and then a rock chick, you can try on Terribly Smart Androgynous and see how you like that, and you can start to learn what suits you and what doesn't.

While you're playing about with this I also suggest getting some cheap basic accessories (belts/scarves/tights/costume jewellery, plain fitted t-shirts), some really well fitting jeans, and some shoes or boots that go with skirts and dresses. Once you've done that it should be much easier to buy one interesting item and be confident that you have the rest of an outfit to go with it.

Also, go subscribe to some fashion blogs (the "outfit photos every day" kind). Make sure they are all from people who are either a) a similar shape to you, or b) a similar colouring to you, or c) have fashion sense you deem to be unbelievably awesome and worthy of emulating. I find that the confidence of fashion bloggers rubs off on me.
posted by emilyw at 6:22 AM on August 2, 2012 [2 favorites]

First of all, don't try to do everything all at once. Most of us started with lip gloss and worked our way up.

I agree with Taff, get your eyebrows professionally done. (I wax my own, with hilarious results.) That's 50% of everything you need right there.

The second thing is to sort out your hair. You'll need a good haircut, not some $8 jobbie at some pop in shop. If you see a good hair cut/style, as the person who has it where they get it done. I've had great luck at the Aveda Institute. I pay $15 for a cut and blow dry, sure it's a student doing it, but if they really screw it up, they teacher will correct it. You'll need to be honest with the stylist about what you're willing to do. If you KNOW you won't blow-dry it, make sure it's wash and wear. (I don't like Aveda products though, much too heavy for my hair.)

With hair and eyebrows, you're ready to conquer the world.

I advocate a B.B. Cream. This is a miracle item that evens skin tone, protects against sun, reflects light and moisturizes. I use Garnier and it costs me about $10 if I get it on sale and use a coupon.

When you're ready to dip your toe into the makeup pool, go to Sephora. They have friendly and helpful people there who can make good recommendations. The one at the mall I shop at has a lovely trans-gender person, if anyone can relate to your issues, I'm thinking a trans-gender person can. I get tips on products, applications and I'm perfectly comfortable saying "I only want to spend X."

Another option you might like is mineral makeup, since it's subtle. It's not particularly cheap though. Maybe you can ask your folks for a gift card for your birthday or the holidays.

Clothing. This one is harder. I'm still not 100% sure of what my style is and I'll be 50 this year! Don't go ape-shit and get the trendiest stuff you can find. Start with good foundation pieces and then add trendy stuff on top. I like In Style magazine, they have neat pages that show trends and how to translate them for different body types and budgets.

The first thing you need to buy for your new wardrobe is a good bra. I'm talking serious money, budget breaking, had to go to a eastern European lady for a fitting bra. I get mine at Nordstrom, but every city and town has a place where bra shopping occurs. Make an appointment and go. Buy the special cleaner, don't put them in the washer!

That should give you a good start.

Hang in there! The gender/sexuality thing is one thing, finding your inner Goddess is something we all struggle with!
posted by Ruthless Bunny at 6:23 AM on August 2, 2012 [4 favorites]

The bunny is correct. Third piece of advice... get a proper fitting by a proper bra specialist for your bra. It's astounding how many women wear a chest size too big and a cup size too small.

(I'm so excited for you, this is simultaneously terrifying and fabulous... and it was for most of us. Woo hoo!)
posted by taff at 6:28 AM on August 2, 2012 [2 favorites]

I know you said you'd look ridiculous with short hair, but I'm going to evangelize for short hair for a moment.

You can only "pull off" pixie hair if you try it! Hair grows back. You're already practical with your morning routine and there are few haircuts more utilitarian and easy to style than a pixie. It is *so* much easier rubbing some cream into a short haircut and giving it a quick blowdry than it is trying to tame a long mane of hair that just wants to do whatever it wants. And I've gotta say, I have never seen a gal look bad with a good pixie haircut. Even on girls of size, even on girls with strange facial shapes or funny features. or glasses.

I promise that a short haircut and the styling advice that fits your hair type will empower you to snazz up the rest of your appearance. Personally, my confidence begins at my hair - if it looks like crap, I feel like crap. If I look badass, I feel badass. Every "new leaf" kind of makeover I've seen on queer girls and non-queer girls started with a daring haircut. There's no one pixie, either - you can go closely cropped or chin length, well groomed and prim or sex-haired and wild, masculine or feminine in style. There are countless Tumblrs out there in praise of short haired women - you should give them a skim!

To summarize, if you want to fit the cute urban queer girl aesthetic, a good short haircut will go a long way!
posted by theraflu at 6:31 AM on August 2, 2012 [4 favorites]

"Your style" is made easier if you first do a bit of reading and work out your body type. Also your face shape. There is an amazing difference to be had with just wearing simple clothes that fit and flatter you. Same with haircuts. No use in falling in love with a particular hair cut if it doesn't suit you.

Here's something I read before knitting my cardigan that actually fit, that is a fairly easy read.
posted by kjs4 at 6:46 AM on August 2, 2012 [1 favorite]

Straight male here, so I have little to offer sadly, but in the flurry of Gore Vidal tributes yesterday, I came across this quote from him about style, reading your question brought it back to my mind, so I offer it here in case its any help:

"Style is knowing who you are, what you want to say, and not giving a damn."

And I'll add that the upshot of this approach is that once you figure out a style that works for you and speaks for you, you can have confidence that anyone who responds to it is responding to you as you can best express yourself. That may take time, but its worth doing. Good luck!
posted by dry white toast at 6:50 AM on August 2, 2012 [3 favorites]

I just want to pop back in to say that I don't really worry about 'being attractive' any more. Partly because I'm older and 'being attractive' in your late thirties is different than in your twenties, partly because I'm a fat butch intellectual weirdo and you must take me as you find me, but mostly because I feel like I look like I am. If you aren't attracted to how I look, you won't be attracted to my personality or way of life and the whole dating/hook-up thing will be a disastrous failure anyway. It saves a tremendous amount of time and emotion not to have to worry about this. (Not that I don't care about specific stuff, like adding a collar pin so that I have sparkle! or buying a fancy new scarf, but I no longer worry about the totality.)

Also it has just really hit me that for the first time in, like, ever I am actually looking forward to wearing the same shirts and sweaters that I've worn for the past couple of autumns rather than hoping for a new miraculous shirt or sweater which will make me feel at ease. This "less churn in the wardrobe" thing is real.
posted by Frowner at 6:58 AM on August 2, 2012 [3 favorites]

I don't think 22 is late to settle into a style. I guess my best advice is to spend some time noticing other people whose style catches your eye, and then try on those ideas.

Don't forget shoes. Find a couple of styles you really love, and then wear the heck out of them. I was looking through old pictures from the years when I was obsessed with mary janes and anything with ankle straps, and dang it if I didn't look adorable. A ladyfriend I knew in NYC varied her style, girly one day and boyish the next, but she always wore this terrific pair of lace-up boots that were her signature.
posted by mochapickle at 7:05 AM on August 2, 2012

I'm almost jealous of you. I gave myself a huge makeover at about the same age, and my life changed overnight. While I'm not queer, the way I present myself often goes against the norms of traditional femininity, but I'm a huge fashion enthusiast all the same.

So here are a couple of things worth knowing about the basics of grooming and presentation, many of which I wish someone had told me years ago. Once you've nailed these, everything else will follow, and you can wear more or less whatever you like with total confidence.

1. If you chose, you can avoid almost all makeup entirely with good diet and the right skincare regime. SPF moisturizer, a regular facial (exfoliating scrubs and/or face packs can work wonders) and appropriate medication for any problems, and all you'll need is a decent concealer for the occasional zit, and possibly mascara and a slash of lippy to keep your mouth looking kissable.

2. But a thousand times Yes! to a great haircut and groomed eyebrows. These are the things that give your face character and define your style, not the slap. And look after your hands and fingernails.

3. Don't wait for your next prescription to find the right pair of glasses. Start looking right away. Have you considered contacts? If you're really short sighted, you might be surprised to discover how your face looks without specs. (I know I was.)

4. You mention big boobs - fer goodness sake, go get fitted for the right bra!

5. Work on your carriage and posture. Learn to stand up straight and relax. People almost never talk about this, but assuming you're able-bodied, it's worth spending a bit of time and money in the right exercise class. Pilates and yoga are great for this.

6. Pay attention to how things fit. Learn a bit about what works for your body shape, and what aspects of your appearance you'd like to accentuate. You can only really learn this by experimenting for yourself, in my opinion.

7. Above all, cultivate confidence. If you think you look great, you probably do. Even when you don't, act like you do with absolute conviction, and you'll be amazed to discover how many people will believe that ridiculous rain hat is actually pretty cool.

Good luck!
posted by Elizabeth the Thirteenth at 7:10 AM on August 2, 2012 [6 favorites]

When I think back over the last 15-20 years of my life, I can mark out distinct phases of style fluctuation. I was very androgynous in high school and college, and then was very butch in my 20s. I turned 30, and despite always having very short, straight hair for my whole life, I decided to see what it would look like if I grew it out. And I coveted the 50s-style dresses that were popping up in stores. I'll be 35 this fall, and I fucking love my long hair (which, it turns out, is curly). I rarely wear make-up, but I love to paint my nails various shades of orange. I have learned that skirts are extremely comfortable in the summer (I am wearing pants today for the first time in weeks), that I like to wear short heels and tall boots (with bright tights), that dresses are the easiest thing to wear ever- instant outfits!
And I feel more like me now than I ever did! It's all me. Even though I have skirts and dresses in my closet, they're all solid-colored and usually dark. I don't like prints. I don't like anything shiny. I don't like large buckles or clasps, especially when they serve no function. My home decorating style is very modern and clean. I feel like I've added my favorite parts of being feminine while retaining all of the best parts of being butch.
So, no, you're not too old to change your style. Make small steps that feel comfortable to you. Trust yourself on it.
posted by aabbbiee at 7:17 AM on August 2, 2012 [2 favorites]

Hello! Your experience sounds so familiar to me!

In my 20s, after I moved to a new city and started really forming my queer identity for myself (rather than defining myself against the people around me and what I perceived to be their expectations), I found myself wanting to change up my image but not knowing how. I felt frumpy and boring and my only relationship to clothes was that I seethed with years of accumulated resentment when I walked past clothes stores.

One day I was watching "But I'm a Cheerleader" again and that scene came up where Clea DuVall walks into the bar wearing a black button-down shirt and I thought "She looks cool! I want to look like that!" So the next time I was forced to go shopping, I got myself a black button down. It did not work miracles, but it looked a lot more put-together than my usual t-shirts, and I felt good about wearing it.

Similarly, although I have never been a jewelry-wearer, a big metal cuff bracelet caught my eye at a flea market some time later and I thought, "Okay, why not?" and bought it. And it looked really good with my black button-down! I started wearing the cuff bracelet with other things, and it became part of my look, and I became more confident about styling myself.

My advice is to pay attention when your eye catches something you find interesting, whether it be a shirt or a piece of jewelry or a pair of shoes or whatever, and give it a shot. Don't try to overhaul your wardrobe all at once - pick up something that looks neat, even if your internal monologue tells you that it's too nice for you, or too cool, or that you are different from the people who are supposed to be wearing it. It will not always work out, but I really think the best way to build a style for yourself is just to try new things, slowly, one piece at a time. The important part is that you should pay attention to and cultivate the little judge of aesthetics inside you who says "I don't actually hate that shirt!"
posted by treefort at 7:20 AM on August 2, 2012 [4 favorites]

"Settling into a style" is totally a myth for most women. Take a look through old family albums- and see what your grandmother wore throughout her life. Heck, talk to anyone over the age of fifty about the fashions they got into.

Clothes and fashion, style and grooming preferences are always an expression of something. If you can work on letting go of the idea that somehow you'll dress/style yourself into being a poser, it would be good. I have read a few tumblrs (maybe I can go find and link one later) where girls spend a month wearing and documenting different hair styles everyday. The girl isn't a poser because she wore a fauxhawk one day, right? And if it looked amazing and she wore it forever after that, she STILL wouldn't be a poser.

The point is, you are allowed to try new things. You should be able to change how you look at will while remembering that in all actuality very very few people are going to notice, and even fewer are going to thing anything negetive. Everyone is too busy getting new haircuts and clothes for themselves.

Also, nthing getting your eyebrows done. It's like face magic.
posted by Blisterlips at 7:32 AM on August 2, 2012 [1 favorite]

Pick up a copy of David Kibbe's "Metamorphosis".

Knowing what shapes and styles work for you will change this whole issue for you. I haven't worn makeup in years. Due to my medical condition, I probably never will again. My recent haircuts cost $3.00. I wear free clothes or thrift store finds, picked up without trying it on first. I get compliments on my hair and clothes fairly often. And it isn't pity. Not everyone realizes I am homeless. I get mistaken for a tourist by folks who would like to sell me touristy services. People read me as very feminine and younger than I am.

Just learn what types of fabric, clothing shapes, patterns, colors etc work for you and you can look great even in jeans and a t-shirt. "Metamorphosis" will teach you that.

Best of luck.
posted by Michele in California at 7:35 AM on August 2, 2012

Everyone here has great ideas. I just want to say that I totally get where you're coming from. I'm not queer but had very similar feelings toward femininity and the projection of self that you do. Your mid-20s is the time for a serious explosion of perspective. It's awesome. Embrace it. I think what's happening is you are realizing that you own your skin. You live in your body and you're not sure but maybe people don't care as much about your personal image as you do. Which is true. It takes guts to shed your former presentation but, really, no one else will hold it against you. And those that do are dealing with their own insecurities.

So, just know this: you live with yourself. Only you get to control your body. You should live in a way that makes you happy and comfortable. Don't hold yourself to this other, insecure teenage standard of yourself who wants to keep you in a box. We ALL have that version of ourselves and it's okay to give her a hug and let her go.
posted by amanda at 7:40 AM on August 2, 2012 [2 favorites]

I expect this is going to resonate with a lot of queer MeFites. I am one of them. I have always had a really complicated relationship to gendered clothing, going back to very early childhood. Dressing myself as an adult was stressful, because I wanted to wear clothes that were perfectly balanced between gender expressions. Those clothes are mostly nondescript, so I wore a lot of t-shirts and jeans.

Here is what changed for me. A few years ago, I realized I was pretty unhappy with the way I looked and my health in general. I stopped smoking. I hired a personal trainer and a nutritionist. I went to a stylist who was better at giving me cool genderqueer haircuts. And I started exploring my personal style. As my body grew stronger, I realized I could wear the clothes I'd always admired—blazers, men's dress shirts, trim fit pants—and feel really good about them. And feeling good made me more confident, so I started curating my look, exploring a wider range of options. Nowadays I use Pinterest, crawl through magazines, and make notes when I see things I like on other people. Even if those other people have been dead for sixty years.

Anyway, I'm not saying you need to change your body to fit your gender expression. It's not even about your body, really—for me it was, but for you it could be anything. I know plenty of dykes and queers of all sizes and shapes who rock an amazing look that is uniquely them. I guess what I'm saying is do whatever it takes to find that inner confidence and work on knowing yourself deeply. That is where the ability to pull off a personal style comes from.
posted by Lieber Frau at 7:54 AM on August 2, 2012 [3 favorites]

I agree with others about eyebrows, a bra that fits...

For makeup, go to Sephora (try to go on a non-weekend) and tell them that you don't know anything about makeup, can't spend a ton, and want basic.
They'll show you how to put it on and are really nice.

For hair, start taking camera phone pix or saving haircuts you like. See if there is a pattern. Ask people in public where they got their haircut. A good haircut is worth spending money on because it lasts longer.

For clothes, get a few nice fitting blazers, jeans, and boots. Rest of your stuff can fit into this.

Good luck!
posted by k8t at 8:04 AM on August 2, 2012

Guy here... and I'm among a vast number of people who are soooooooo glad we've evolved past our early-20s styles ('cause we had absolutely no clue and cringe and laugh when we see the old pictures).

Operationally, lots of things to be tried out via thrift-store purchases.

And do have some fun with it.
posted by ambient2 at 8:13 AM on August 2, 2012 [1 favorite]

"But I guess my real question is, though, how do I not feel so ridiculous trying? I spent my entire adolescence acting either aggressively opposed to this sort of stuff or innocently too "deep" for it. It's a big part of who I was, which is probably why it feels like such a big deal changing it. "

I think many, many women (straight or gay or otherwise) who spent their adolescence feeling that way, or just ignoring it, feel "ridiculous" when they start trying. I guess it stops feeling ridiculous when you stop feeling like you're trying, you know? Why you find something that works and start to feel good in it instead of like a kid playing dress-up. Which just takes a while.

Do you have a friend who likes to shop who has a style you admire? (Not necessarily the style you want, just that she looks great for her.) Ask her if she'll go shopping with you, that you want to get a couple of outfits for "going out dancing" or "work meetings" or "looking chic at yoga" or "saturdays getting coffee and scoping girls" and that you want to try something different and need some help. "I always just pick out the same things that I know are comfortable, I never even thing to TRY anything else, so I've been having trouble picking out some new things!" You have a great shopping day, pick out a couple adorable new outfits with help from your honest-but-fun friend, and then when you go to put on your new urban chic saturday coffee outfit and you feel awkward about wearing a fitted top and cute pants, you remind yourself, "Friend said I looked FANTASTIC in this, so I know I'm not going out looking like a dork. I'm just not used to it. I have outside confirmation that I look great! I can do this!"

Friends are great for helping you pick out things you'd never try otherwise (I never tried on V-necks until I had a friend personal-shopping for me one day when I was frustrated trying to find shirts ... I guess I thought they were for girls with boobs or something and I didn't grow any until I was in my 20s -- I loved them!), and then give you reassurance that it looks good on you, because it's hard to be sure when you're trying something new. And they tell you, "It's a great skirt, but the seam wrinkles over your butt, I'm sure we can find something that length that's better-made, in the same color scheme," or "You know, I think a tailor could fix the way that jacket lies."

Also having a friend makes the tediousness of shopping less tedious.
posted by Eyebrows McGee at 8:32 AM on August 2, 2012 [1 favorite]

On glasses: Why wait for a new pair?

If you've got a relatively simple prescription, you can try out lots of fun styles through places like Zenni Optical for very little. I just bought three pairs for my daughter and spent $50. I bought myself a set of mid-focal computer glasses and some Ray-ban-copy sunglasses for $20 total.

There are lots of online glasses vendors, frequent coupons, prices as low as $7 shipped. No reason to stick with "dorky" glasses. MeMail if you want links and more information.
posted by chazlarson at 8:37 AM on August 2, 2012 [2 favorites]

I'm a straight woman and I can relate to a lot of what you say. When I was growing up, I didn't like what was seen as 'attractive' around me - I didn't like the clothes, the make-up, the blonde hair dye, the hair-gel, the fake-tan. Partly because I didn't like the way I looked and didn't think I would look any better and didn't want to try, and partly because it was a game I didn't want to play - I didn't want to dress a certain way or wear shoes I couldn't walk in because it was expected of me - I too read The Beauty Myth and I didn't like the idea that you 'should' do all that stuff to be considered normal. I was dimly aware that you could be an individual and feminist AND dress up a bit, but I didn't know how, because all I saw were people looking the same in clothes I didn't like. It was easier to wear cheap men's jeans and flannel shirts and not think about it too much.

I wasn't interested in clothes for a long time, not until I made regular trips to and then moved to the big city and realised it wasn't that I wasn't interested in looking good, I just wasn't interested in 'looking good' in the way other people did. I realised there were things I liked, that I liked wearing make-up to look interesting rather than to try and look like Pamela Anderson, and eventually I worked out what I liked. I didn't wear many dresses and skirts a few years ago, but I realised they fit my shape much better than trying to get my big bust into tops - this is something that takes time and people change their styles all the time because their circumstances, bodies and tastes changed. I knew from a young age that I didn't have to like something just because it was fashionable, and I learned that it wouldn't suit me just because it suited everyone else. Recently I've been looking at blogs like Already Pretty or with people that dress full-time in vintage clothing, and I love the way blogs show us what real people wear and look like rather than the fantasy image you get in magazines of an airbrushed woman in shoes that look great because a woman in a fashion shoot never has to run for the bus or stand in the rain. (I still feel like a drag queen in heels.)

You don't *need* to pluck your eyebrows or wear make-up or wear a floral print to be pretty - it sounds like you know that already - but it's fine to try them out and see if you like the effect. And if you don't, you're still pretty.
posted by mippy at 8:37 AM on August 2, 2012 [1 favorite]

"Also, I feel like most other people have settled into their style by this age even if do they switch things up here and there, so this sort of deliberate change feels kind of life-stage inappropriate."

I just wanted to add, a lot of intelligent women are later bloomers on things like style and fashion. You're at a really normal age to be figuring this out. I didn't start dressing myself non-sclubbily until I was in college, and I basically had to dress both my college roommates for their med school interviews (at age 22) because one had never owned any shoes that weren't cheap sneakers and the other never wore anything but jeans and T-shirts and felt embarrassed about being in anything as close-fitting as a suit. They're both chic professional-looking doctors these days in very stylish clothes that suit their personalities. In law school I had several friends still in the "sweats and jeans and Ts" phase who were awkwardly trying to learn to dress. A friend of mine is prominent in fashion and gets photographed at NY fashiony events being fashionable, and until she was 30 it was ... well, it was bad. There were hammer pants and denim, at the same time.

Anyway, you're in good company. It's a good age to be figuring this out. Lots of us do.
posted by Eyebrows McGee at 8:39 AM on August 2, 2012 [1 favorite]

I've internalized patriarchal beauty standards enough to only be attracted to women who mostly fit them (yeah, stone me).

Don't feel bad about this. We all internalize beauty standards. Sexual tastes are politically incorrect, which makes them guilt-inducing and exciting at the same time. And you can't run away from them.

It sounds to me, though, that in order to attract women who fit this profile, you should butch it up, adapting the extremely useful comments in this thread into a totally personal, distinct, and awesome butch presentation.
posted by Gordion Knott at 8:43 AM on August 2, 2012 [1 favorite]

Also, writing that reminded me of something.

I've been reading up on perfumes lately and thinking about how smells can make one feel like they're in a costume or makes them feel more mysterious or cute or giddy. I have a Le Labo (unisex) scent, Patchouli 24, which smells like smoke and vanilla and old books and makes me feel a bit sharper and a bit more mysterious. In my teens, I wanted to be that smoke-vanilla-book girl but I was torn between not wanting to be a dewberry-musk girl like the others but not knowing what other options there were, and feeling like I should be.

Thinking about perfume reminds me of how I used to feel about fashion/style. Most of the stuff in Boots smells like fabric conditioner to me, but if you have a retailer of 'niche' perfume near you, it's worth exploring. You can offset a pastel colour, for example, with a men's cologne (Old Spice is surprisingly feminine). There are perfumes out there that smell like jasmine with cigarettes, beetles (BPAL comes up on the Metafilter forums a lot) and, let's not mince words, cum. What you're doing here is the style equivalent of 'I want to smell nice, but I don't want to smell like Britney Spears Radiance'.
posted by mippy at 8:46 AM on August 2, 2012 [2 favorites]

Hey! I am a 26 year old lesbian and have been working on the same problem for the last couple of years. You are not alone!

Get an exciting haircut. It doesn't have to be short (but if you've never tried short before, you might be surprised, so give it a shot) but it has to be really good and a change. Ask around, get the name of a good stylist--it's important to go to a specific stylist, not just a salon in general--and spend some serious cash if you need to. A haircut can change everything.

Don't be afraid to not wear makeup if you don't like it. It's a good idea to try, but it's not necessary, either. I'm pretty femme, but I don't wear anything but clear lip gloss on a daily basis, with mascara for very special occasions. It's really not a necessity. (But of course, if you like it, go for it.)

You might want to test-drive both femme and butch looks. I've enjoyed experimenting with both, and now I am loving a place in the middle, with the femme sundresses and butch combat boots. There's something to be said for buying lots of cheap clothes in a variety of styles for a while so you can try things out; once you've experimented, you'll be better able to choose more expensive pieces that you'll want to wear for a long time.

The suggestions above for fashion blogs and tumblrs are spot-on. Looking at people you see out at clubs or whatever with an eye to "would I look good in that?" is helpful, too.

Going shopping with a friend is great if possible. If it isn't possible, find a shop with a style you want to try and go when they're not busy. Start trying on a lot of things by yourself, and quite likely the salespeople will get in on it and pick things for you to try, too. It's really good to get someone else's eye involved, even if it's not someone you know. (And of course, you don't have to buy what they suggest--it's just to get you into some things you wouldn't usually think to try.)

Also, have fun!
posted by snorkmaiden at 8:51 AM on August 2, 2012 [1 favorite]

RE: Makeup, If there is a Sephora near you I would go there. Maybe pick one or two things that you want to try (foundation, mascara, etc) then go there and ask for some help. You can tell them, "I've never worn makeup before and I'd like to start. Today I'd like to find some mascara and foundation." I just picked those two at random so you can feel free to start with something else (and they might make a suggestion).

In the few weeks before we got married, my wife went there and told them almost the same thing, "I've been wearing makeup for years but I don't feel like I know what I'm doing. Help me." She was that employee's favorite person for the next hour.

The point is, there are plenty of professionals out there who would LOVE to help you out.
posted by VTX at 8:57 AM on August 2, 2012

First of all, in my thirtieth year I quit my job and moved across the country so I could have the freedom to explore who I wanted to be instead of performing to others' expectations. Sometimes it's hard to even sort out what you want vs. what others expect. You are not too old!

how do I not feel so ridiculous trying?

Maybe you can re-frame the whole makeover issue as one of honoring yourself, exploring your own identity and image, and doing things to look good because looking good makes you feel good. I sense there is a little self-esteem stuff at play here. You deserve to look awesome and feel awesome, okay? Also, you might see what it feels like to think of your experimentation as a form of gender play, rather than some betrayal of queerness and feminism. It's 2012 and call me Pollyanna but I like to think part of what feminism and LGBT movements have accomplished is winning us all the freedom to choose how we want to present ourselves and live our lives.

When it comes to actually trying new hotness tactics, go slow and experimental. (I hope this isn't rude but I am reminded of when straight-identified men have cross-dressing interest and they start out by, say, wearing a feminine scarf as a pocket square, and then maybe change up their underwear, instead of just busting out full drag in one fell swoop.) Great advice above to try a new hairstyle early on. Maybe start wearing a fragrance you like and see how that makes you feel? (Can be girly, masculine, or somewhere in between. Dig TokyoMilk.) You could swap out your moisturizer for a tinted one to help even your skin tone with no extra effort. Mascara (or an eyelash tint) and lip gloss can make a big difference without making you look "made up." There is fantastic advice above about paying attention to how you feel each step of the way, and following what feels authentic.
posted by TrixieRamble at 8:59 AM on August 2, 2012

Just thought about it, and I have one more thing to add to the list, and it's also one of the hardest things to learn:

Do not shop indiscriminately. Sure, you can experiment with inexpensive stuff, but when you know what you want, it is absolutely worth hunting down the perfect leather jacket, the finest button down shirt, that pair of artisan-quality shoes or whatever the classics are that fit your particular personal style. It takes time to work out what you need, but be patient, cultivate an eye and learn how to stalk those pieces you know you'll really love.

Great wardrobes are like Rome. They aren't built in a day.
posted by Elizabeth the Thirteenth at 9:11 AM on August 2, 2012

You know, upon re-reading a lot of the responses - including mine - I realized that some of us are kind of conflating "hot" with "femme"...sorry about that! It sounds like what you really want is A Style, not necessarily a more feminine one, just a more distinctive look that involves some effort and deliberateness. Of course as you are trying new looks/scents/grooming/clothes, try anything and everything that appeals to you! Maybe your personal look will turn out to be feminine dresses, or maybe it will be metrosexual (do people still say that?), or who knows what. Have fun!
posted by TrixieRamble at 9:15 AM on August 2, 2012 [1 favorite]

Don't feel ridiculous about wanting to have fun with your clothes and your grooming! I am with Emma Goldman in not wanting a revolution if I can't dance. Or wear fabulous scarves.
posted by Sidhedevil at 9:18 AM on August 2, 2012

I started doing this around your age, so you're by no means alone or behind the curve. I dressed very sloppy butch in college; my model was my fellow male CS majors who lived in ratty jeans and free t-shirts. After I graduated, I also realized that I wanted to look good without having to compromise my feminist values. It took something like six years, but I eventually developed an androgynous style that skews femme. Here are the things I wish I'd known when I started:

Try everything. That super short haircut you always sort of wanted but were afraid would make your round face look rounder? It looks amazing on you. It brings out your eyes and cheekbones and makes you more you. Go find a hair salon that caters to LGBT folk and have one of them sort you out. If you live in or near San Diego, I can recommend someone who is an absolute genius at cutting hair for lesbians.

No, really, try EVERYTHING. When you go shopping, don't just make a beeline for the most practical or cheap items. Walk through the whole store, grab everything that catches your eye in a couple of different sizes, and put them on. Go to Sephora and do the same with makeup. Walk around a department store and hold up as many earrings, necklaces, watches and bracelets up to your face. Whenever you see a style you like, make a note of it and look for stores that cater to that style. Eventually, this will teach you what proportions and colors look best on you and shopping will be much easier.

Be very particular about fit. This means: no lumps, no awkward gaps when you bend over, no needing to tug on parts all the time to make them look right. When it comes to jeans, buy the ones that fit at the waist and hips. You can get the rest taken in and shortened to fit. If it doesn't fit right and make you feel confident, don't buy it. If it highlights your best features, buy it.

Have a good foundation. This means buying underthings that fit well and look smooth under your clothes. So you will probably need several bras with different strap styles, as well as having a selection of nude bras. I wish someone had told me that dark skin + white bra + white shirt = everyone can see your bra. Yes, I was that clueless.

Have a good, large mirror.

I'm sorry, things are going to be awkward for a good long while, so get used to it. You will end up trying styles that look terrible, styles that don't make any sense on you (huh, really, full face of makeup doesn't fit this DIY tomboy's personality? whodathunk?), and styles that look great but feel odd on you. You will feel weird about people checking you out, because yes, you are now dressing up enough to get that kind of open attention. You are going to feel ridiculous, a lot. But--once you start to get good at it, you're going to feel really damn good. And confident. So, it's worth it.

Finally: You like what you like. The current model of woman approved by the patriarchy wouldn't be considered attractive in other eras and other cultures. You may have been programmed to be attracted to this sort of woman, but it's just as likely that this is your type. I am attracted to people who fit the "conventionally attractive" mold, but I was surprised to find how many people told me that the person I thought was hot hot hot was average looking to them. Sexual attraction is way more complicated than checking off a list of features, so don't beat yourself up about it.
posted by rhythm and booze at 9:38 AM on August 2, 2012 [6 favorites]

Someone's comment makes me think my post might be misconstrue because of how I worded it. I am not suggesting you need to be femme. I am suggesting that understanding what lines, material weights, etc work for your body type will make you look good regardless of the type of personae or style you want to go with. Just in case I failed to make that clear.
posted by Michele in California at 9:47 AM on August 2, 2012

I'm a 27-year-old dyke, and I learned to apply makeup in the past 6 months. These videos were incredibly helpful, as was asking an ex-girlfriend for help while shopping.

As for the guilt over caving to societal expectations of beauty, I totally understand that. It's why I didn't wear makeup for so long. But I think we get a unique opportunity in the queer community to play around with expectations. You can take certain aspects and leave out others. You can play dress-up. It's OK to take a while to get it right.
posted by a hat out of hell at 9:52 AM on August 2, 2012 [3 favorites]

You sound adorable!

I live in a city with lots of 20-somethings who look great and vaguely androgenous. I study them, trying to figure out how they do it. I think you could easily achieve something that makes you look put together and hot, but that doesn't look like you tried too hard. You really don't have to go out and buy a bunch of trendy clothes that you wouldn't normally look twice at, as you put it. Getting dressed should be an adventure in self-expression, and it should be fun! I think you can look wonderful without having to go trendy, overaccessorized, or Barbie-ish.

If you can't stand accessories, go sleek and simple. Here's a look I've seen on the street recently that I really love: straight-leg black pants (the skinny black jeans like Rudes, or the fuller-leg twill "janitor" pants style), black retro sneaks, and a simple shirt in any color. A sleeveless Fred Perry-type golf shirt in navy would be really crisp yet pretty.

You mentioned your chest size - if you're in the least self-conscious about this (and you shouldn't be, but we all have our issues and I can relate to this one), get a bra fitting at a lingerie or department store, and/or buy some bras that feel good and look seamless under your clothes.

Short hair is incredibly versatile. Just push it around with gel and see what you like. Try smooshing it straight back off your forehead and behind your ears so your cheekbones are showing. Cheekbones are hot :) Set them off with a pair of gem stud earrings in your fave color, maybe.

Keep doing the spf moisturizer. Foundation's too much at your age - no need to obscure your fab 20-something skin! But you can use tinted moisturizer to even out your skin tone for date nights or whatever. Some clear lip gloss will give you a finished look, and it'll keep your lips soft too. Vaseline works great for that - it comes in tiny little jars you can carry with you.

Not everyone likes scent, but I do - sometimes I wear soemthing very subtle that no one else can even smell but me. It just makes me feel good. There is every kind of scent out there you can imagine. You don't have to stick with fragrances marketed to women - men's fragrances are amazing. My dad used to wear something called Aramis - I've worn it too and I love it. Anyway, explore and have fun!
posted by cartoonella at 10:22 AM on August 2, 2012

But I guess my real question is, though, how do I not feel so ridiculous trying? [...] I don't have any real reason to believe I won't just feel like a potential poser again

First step: kind to yourself. :) I view dressing up and being well groomed as taking care of myself, so that I may be the best version of myself.

I love Garance Dore's blog because of posts like this. I can't recommend her blog highly enough--there are fifty million fashion/style blogs out there, but I believe she's probably the only one talking very frankly about the pressure to conform (she moved from Paris to NY), being in a style rut, and experimenting with different styles.

Also, I feel like most other people have settled into their style by this age even if do they switch things up here and there, so this sort of deliberate change feels kind of life-stage inappropriate.

Oh, no. So few of us have money to spend on clothes and grooming straight out of college. Maybe I'm a late bloomer with fellow late-blooming friends, but the general consensus is that we pretty much started to settle into our looks and a personal style we're comfortable with in our late twenties. (Having a little more disposable income is a major factor.) I'm in my early thirties and I'm still looking to reboot my wardrobe.

Clothing wise, one of the first things you could do is to start wearing things that fit a little more closely to your body. This almost immediately "urbanizes" your look. For instance, when it comes to jeans, adopt those with dark washes in a slim-straight (or skinny, if you dare) cut.

As for makeup, if your skin is in good condition, you need nothing more than a tinted moisturizer, mascara, blush (if you're pale; cream blushes are super easy to apply and sheer out), concealer, tinted lip balm or gloss/sheer lipstick and concealer to begin with for a polished, no-makeup look. Your youth will take care of everything else. Be sure to use sunscreen--it's a health issue, not a beauty one--and always take your makeup off at night.

By the way, I think it's a great time to develop a personal style! There are so many fashion and street style blogs to look at right now, and so many ways to scrapbook them online (Polyvore, Pinterest, Tumblr but be careful of copyright issues).

Here's a few of my favourites:

Nerd Girlfriend

Bonnie Tsang's Pinterest, which I like because it's feminine but not girly.

The Man Repeller

Le Blog de Betty

Keiko Lynn

Nerd Boyfriend

Tomboy Style

Stockholm Street Style

All the best!
posted by peripathetic at 10:32 AM on August 2, 2012 [11 favorites]

... and Well And Dapper.
posted by peripathetic at 10:34 AM on August 2, 2012 [1 favorite]

how do I not feel so ridiculous trying?

I totally get where you're coming from. I'm a middle-aged version of you. What has worked for me is to not approach in terms of "new image!" but in terms of new bra. New haircut. New glasses. New flattering jeans. Get the basics going and then it becomes easier to add things in. Once the glasses and the haircut are in place, then it's easy to find the earrings. Once you have the jeans, then look for shoes that look great with them. Good luck and have fun!
posted by Wordwoman at 10:41 AM on August 2, 2012 [1 favorite]

I DO NOT feel hot in girly clothes. I feel silly. And I am a 40-something straight woman. I feel like I am playing dress up and want to go home.

I feel sexiest when I have been taking care of my body-- mostly running, Yoga or pilates.
It's amazing how I feel sexy and confident when I take care of my body.

That being said the things that make me feel "hot"

Well groomed eyebrows
a decent hair cut
Fitted clothes (when I wear baggy everything like I am prone to do I feel slouchy)
Good posture
A favorite piece of clothing
Eating well (low carbs makes me feel lighter, kickier)
having clear skin (or appearing to with a dash of concealer and blush/bronzer)

(If you want to make a wardrobe change I suggest Salvation army especially on half off day. You can literally get a wardrobe for 15 bucks [not shoes, tho really]and if you decide it's not you, you can't donate it back and go for another look).

Good luck
posted by beccaj at 10:43 AM on August 2, 2012

Nthing Autostraddle; the fashion section is good. also check out tomboy femme. I also watch The Real L Word primarily for the LA lesbian fashion (and I have such a crush on Whitney); lots of inspiration there (drama aside). It makes me want to get tattoos and shave part of my head.

It took me a long time to figure out my style. I was uncomfortably femme for years. I don't wear makeup, but I do pluck my brows (when I remember to, ha) and wear red lipstick occasionally. I have a pixie cut and don't shave my pits; I wear things that make me happy; people can't really fuck with that. I usually have some sort of uniform that I cycle through. I've been trying to buy investment pieces rather than trendy stuff.
posted by hotelechozulu at 10:44 AM on August 2, 2012

It's 100% life stage appropriate - at 22, you're still figuring out who you are, and most people go through some changes then. My style changed then, and still changes! You might not feel comfortable right away, it's something different than you're used to feeling about yourself, and that's okay! Just see what you like, and have fun with it. And I think everyone feels like a poser at least sometimes.
posted by mrs. taters at 11:27 AM on August 2, 2012

I'm a straight woman, and I had huge problems with gendered standards of clothing and beauty for most of my growing up years. I had defined myself as someone who never wore dresses or skirts or anything girly, to the point where, by graduation, I felt trapped in an image that didn't fit.

What got me out of my shell was going to college and living with a group of women, all with different styles, who all wanted me to borrow their clothes (because my own were so awful). My freshman year was just one giant game of dress up. At the end of the year, I had a much better idea of what I liked and what looked good on me, and I had not spent a ton of money.

Now, you're out of college, but do you have friends who are approximately your size? Maybe well dressed friends whose style you might like to imitate? Would they be willing to help you dress for a night out and let you test-drive some new looks?

And if there's someone you really trust, take them shopping.
posted by oryelle at 11:57 AM on August 2, 2012

Have you read the bra post? Read it. Be not afraid. Follow the methods it describes, and go to a good bra store (eg Nordstrom) to try on in person.
posted by LobsterMitten at 11:57 AM on August 2, 2012 [1 favorite]

Two things that caught my eye here:

The last time I really dressed up girly was a couple years ago and I felt like I was in drag

:/ No fun. But consider some wise words from RuPaul: "You're born naked. The rest is all drag." Maybe the way forward is to think of what you're doing here as looking for a flavor of drag that you DO find fun to wear.

I've internalized patriarchal beauty standards enough to only be attracted to women who mostly fit them (yeah, stone me).

No stoning here, it sounds like you're stoning yourself more than enough already! What happens if you try to cultivate in yourself some things that you find attractive in other people? Applied to either style or confidence or whatever, that's a strategy that has occasionally helped me in my efforts to be awesome.

And on a practical note: as an end run around your hair quandary, what about wearing it shorter than chin length in the back, but longer in the front? Looks good sleek or messy or asymmetrical, and is totally conducive to your target cute-urban-queer-girl aesthetic.
posted by clavicle at 12:09 PM on August 2, 2012 [1 favorite]

ETSY!!!!!!!! Cheap, cool clothes.

Plus you're gonna experiment with styles. See what you like. Window shop.

In terms of the feelings, blitz through them. I started wearing pretty wild things, and it made me nervous. You know what happened? People constantly complimented me on my clothes. All of the time. Needless to say, I got over it.

Also never, ever forget accessories. They make the show.

Hair, you're on your own, I'm a guy who has very little.
posted by Ironmouth at 12:43 PM on August 2, 2012 [1 favorite]

Ok you.

The easier stuff.

Haircut first. Nthing what all the smarties have said before. Get a good one. Do not go cheap on this. Get something trendy. Look at lots of pictures and see what you like that have different kinds and then talk to someone about what would work with your hair. And keep it up, regular appointments.

Then new glasses after new haircut. No need to wait for a new prescription.

Clothes...well I'm a lesbian to the femme side of the middle. But I mix it up a bit with clothing. Sometimes I'm a little more girly and sometimes I feel strong and sexy in jeans and a tshirt. Look around and see what you like on others.

Makeup...I would go slow on this one and just experiment. I rarely, rarely wear more than mascara and a little powder and my lady wears chapstick. Also agree with the eyebrow shaping.

Also know that you don't have to go with one permanent look all the time. You can completely mix it up depending upon how you feel and where you are going. But haircut *can be* hard to change up so I would give that the most thought. But you can change it. This is the time for exploration!

Lastly, how do you feel the confidence? I think you might be surprised in how it just happens. Taking care of yourself in this way, looking in the mirror and feeling good about yourself, will just inspire these things. If you make a mistake, you can never wear that shirt again. If your hair is a disaster, it will go. You can be proud that you are making attempts to express yourself. And as you make these changes, you will begin to find your look and your way. And hopefully your outside will match your strong inside, yes?
Best of luck to you. Sometimes, you just got to make the jump.
posted by Kitty Cornered at 12:57 PM on August 2, 2012 [1 favorite]

Aside from the hair/brows/bra advice others have given (omg the bra thing is SO CRUCIAL), I think you should start with more fitted versions of the types of clothes you normally wear! That way, you'll look more feminine without actually radically changing your style.

I played around on Polyvore (which I HIGHLY recommend, so fun) and made some outfits that you might consider. All of them are entirely composed of pieces that a guy might wear- jeans, boots, Oxford shoes, tees, button-downs- but in more feminine cuts. You could start dressing more in this vein, and then slowly add accessories, girly colors or skirts/dresses as you begin to feel more comfortable with dressing up. Or, hell, maybe you'll stick with androgynous pieces forever, and that's fine too!
posted by showbiz_liz at 1:30 PM on August 2, 2012

For a bit of a meta look at what you're dealing with, read the anthology It's So You (edited by Michelle Tea, one of my personal icons). Women representing a range of ages, professions, class backgrounds, gender presentations, sexual orientations, etc., talk about how they've struggled with the whole clothing and "beauty" thang and how what they wear does (or does not) reflect who they are. I've made this book sound terribly earnest and academic, but it's actually funny, raunchy, sad, and sexy by turns.

As for your having reached the age by which "most other people have settled into their style": You haven't. (She says, joining the chorus clamoring to make this point.)

I'm 47, and I was so traumatized by having come of age when preppie clothes/Farrah hair were all the rage that I'm still settling into my style! As a bisexual woman with an hourglass figure, a crooked nose, and massively thick and curly Mediterranean hair, I was never going to rock a look comprised of layers of oxford-cloth shirts, turtlenecks, and Fair Isle sweaters, topped by a head of blow-dried and feathered bangs. But of course I blamed myself when this combination -- over and over again -- proved not to flatter.

It would've helped to know that someone, somewhere, thought it was OK for me to let my freak flag fly. If only this declaration (by Lester Bangs, musician and music journalist) had come across my radar screen sooner*: "Style is originality; fashion is fascism. The two are eternally and unalterably opposed.” Words to live by.

* In the pre-Internet era, life-changing wisdom such as this was much less accessible. Sigh.
posted by virago at 2:01 PM on August 2, 2012 [2 favorites]

I wpouldn't get a trendy haircut first off, because if you don't know how to make it happen at home, it'll look pretty strange. I got my hair cut as a student at a popular fashion-led chain here, and not only did they ignore the fact I wear glasses (meaning I was constantly clipping it back) but it was a style that looked great for someone who knew how to blow-dry at home, less so for me who didn't own a hairdryer until she was on the way home from the salon.

However, it takes a while to find out what works and a hairdresser will help. I have very flat, straight hair and getting a bob works for me. Bobs can be fairly androgynous if you want them to be, as well - look at Justine Frischmann, a straight girl who played with androgyny and wore leather and Doc Martens. Dye can turn it femme (highlights and such) or butch (dark colours, punky colours) if you like too. At a time in my life when I felt like everyone was staring and me and whispering, I bleached then dyed my hair pillarbox red and from then on if they stared at me, I felt like it was because of my awesome hair, and the self-consciousness disappeared. Bright dye might not viable if you work in a corporate job, but doing something that feels different or outrageous can work in a similar way.
posted by mippy at 2:16 PM on August 2, 2012

Do you ever see anyone and think "you know, I wish I had his/her style"? Copy them! Copy them shamelessly. I saw a girl on the subway wearing a smart blazer with cutoffs, and I actually went home and put that outfit on to go out for the night because what, she has a trademark on fun clothes? No one does! For a while, I was secretly obsessed with one of my coworker's style, and when I'd try clothes on, I'd think "would Nicole wear this?" Not, you know, a head-to-toe copy necessarily, but would she put something like this together? She was really chic, and at the time I was more "I have many, many Threadless t-shirts," and I wasn't sure how to go from my post-college stuff to the more professional/artsy style.

Here are two of my favorite fashion blogs right now that I think might fit your aesthetic, or at least get some of the wheels turning: Faintly Masculine and Tomboy Style.

Finally, I can't emphasize enough: You are never late to have style, and it's not shallow or pathetic to want to feel good about the visual story you tell about yourself when you leave the house in the morning. It's always good to enjoy the things you actually enjoy, and to be kind to yourself, and to take yourself seriously, and to not take yourself too seriously, and to try new things. Your early 20s are a time of major change as it is, and that means it's extra legit to shake-up your style. Everyone's style evolves. There's absolutely nothing ridiculous about wanting to look however you want to look. Trust.

[and feel free to memail me if you want more fashion chitchat or to hobnob about "should I get a vest?" or whatever. I love it so.]
posted by Charity Garfein at 5:41 PM on August 2, 2012 [1 favorite]

Don't beat yourself up. I'm in my late 20s and a straight feminine-presenting lady, but I still struggle with gender expression, etc. I was the smart kid in school and while I did care about clothes, I didn't wear makeup and I usually dressed pretty conservatively (in terms of colours/fit/etc.). I have just started wearing makeup/nail polish regularly in the last few months and it is really weird for me, mostly because whatever political feelings I have about compulsory femininity, I still like lipstick and nail polish and basically didn't wear them because I was worried about looking stupid. It's complicated. It's a process.

You don't have to do any of the conventional wisdom things if you don't want, but I promise you will be happier about your hair if you spend semi-serious money on a haircut you like - go to a good stylist. You can get cheap makeup, you can get cheap clothes, but you have to wear your haircut all the time time. Also if you want new glasses, just get new glasses. Read fashion/beauty tumblrs and blogs (tumblr is super-great for this because you can find lots of queer and straight ladies overthinking their gender expressions and embracing less "mainstream" looks and who aren't necessarily trying to sell you stuff, frowner is definitely on the right track) - there are loads, some good suggestions have already been made. Add things in little by little. (For me, I started wearing grey nail polish and then slowly added lipstick when I went out, and then other stuff - now I'm wearing more-or-less full makeup to work most days. So far no one has made fun of me. I still don't really understand foundation, but tinted moisturizer is hard to mess up.) When you see something you think looks good, do that. Add in accessories, try out colour combinations you've never worn before, stuff like that.

Also, I hope this makes sense, but don't stress about finding stuff that feels like you - go to stores and try on stuff that is new for you. I'm not saying go out in stuff that makes you feel uncomfortable, but I am saying don't worry about finding stuff (clothes, accessories, make-up) that's the most "you" - try stuff on and see if it could be you. Clothes wise I have a pretty defined style (mostly striped boatneck tees and bright colours) but I still am always finding out that stuff that I didn't think could ever work for me actually works for me.
posted by SoftRain at 7:04 PM on August 2, 2012

I agree with everyone else about baby steps. Just browse through the Internet to find styles that appeal to you (Pinterest is particularly excellent for that sort of thing). As someone who does not identify in particular with "girly" styles but still wants to look like an attractive lady, I am constantly drawn to styles that emphasize feminine menswear (example 1; example 2; seconding the Tomboy Style blog linked above). This sort of look can be achieved via Value Village/consignment/second hand + tailoring. Someone above also mentioned Etsy: it is so great.

But as a lot of people have said, just experiment because people go through styles constantly! That's precisely what the fashion industry capitalizes on. And have fun. As you know, genders don't have to abide by strict norms - and neither does style.
posted by thebots at 10:52 PM on August 2, 2012

Hello, me. Down to the "it's not feminist to be stylish!".

I second all the recs for femme resources - even if you don't identify as femme, that subculture has done a lot of thinking about the politics of fashion and how to be stylish and ethical. I wrote a FPP about femme culture on the Blue that you may find useful.

(heh, garconierre is a friend of mine :))

As for emulating role models: don't be afraid to look outside your gender. I am a massive fan of Darren Hayes and rather like this artsy dapper thing he's got going on. I'm thinking of ways to femme-ify it.
posted by divabat at 9:54 AM on September 4, 2012 [1 favorite]

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