I’m a 50 year old man who would like to present more feminine
October 9, 2018 10:26 AM   Subscribe

In the last month I have become aware that I identify significantly as female and I am looking for ideas to present slightly more female, though it will be enough for now if I am the only one who knows it. I am looking for ideas (ie what sort of clothes to buy or how to wear them) and any other resources.

I’m laughably cis-het: 6’1”, fit, big and strong, married with two kids at home. I work in New York City a straight field - think fancy law firm - but just work with one junior colleague most days and can wear what I want, though the suit will still have to come out of the closet (heh) once in a while.

This is only a few weeks old for me. What I want is to present at work and off more softer, prettier, more open and feminine. Most of my wardrobe is blacks and grays, and I would usually wear a suit or wool pants with a fancy button down shirt to work. All I have done so far is to buy some form fitting pants and open an extra button on my shirt an extra button. It’s small potatoes but it feels good to me even if no one else notices. I have also thought about getting more colorful clothes but then there is a certain southern frat dude who wears brightly. Colored shirts and I don’t want to look like that. The only other thing on the horizon is jewelry, I don't wear much but I have also been looking at some feminine bracelets to wear.

I think one classic thing to do is wear women's underwear, but that doesn't do it for me and I upgraded my underwear a few years ago and it is already pretty.

As far as other resources, they might be helpful too. Most of the easily findable stuff is geared toward cross dressing or people who want to fully present as female and I don’t want to (yet).
posted by anonymous to Clothing, Beauty, & Fashion (42 answers total) 14 users marked this as a favorite
Cashmere sweater.
posted by sammyo at 10:30 AM on October 9, 2018 [5 favorites]

Perhaps trying some of these changes/items (not all at once of course:)

Softer textures
Fitted silhouettes
Extra details (accent buttons, zippers, etc.)
Decorative scarves
Oversized, brightly-colored bag or tote
posted by jraz at 10:39 AM on October 9, 2018 [2 favorites]

What about expanding the colors/patterns you wear for your clothes/accessories beyond just the shirt? As the weather gets colder, maybe scarves in more feminine colors or patterns? Or colorful or patterned socks?

Cardigans to wear with the fancy shirts and wool pants? They could be "men's" cut but still feel a little softer and more flowy.
posted by aka burlap at 10:42 AM on October 9, 2018 [1 favorite]

I, too, wore a lot of fitted pants and left a button undone on my dress shirts in my early stages of presenting more femme. I love the way necklaces can add to that. Today, I'm wearing a simple rectangular gold pendant on a slim chain.

It's feeling like fall over here, so wearing a longer sweater in a tunic length is a nice gray area as well.

Shoes can be a nice addition. On the dressier side, I have a few from Stacy Adams that even have a bit of a heel.

I'm also a fan of tinted lip balm. Burt's Bee's Red Dahlia is subtle on me. Huge boost to feeling femme but slips right under the radar of most cis men.
posted by advicepig at 10:43 AM on October 9, 2018 [16 favorites]

I can't really tell if you want to put your new look together from things branded for men, or if you are willing to cross the aisle. When I first dare cross the aisle, I went to Gap and Banana Republic because they don't gender dressing rooms. I'd carry what I wanted to try on with a pair of jeans on top so it didn't look too gendered. It helped to get a sense of what sizing worked for me.
posted by advicepig at 10:46 AM on October 9, 2018 [2 favorites]

If your climate allows it, sweaters is where it's at. Bulky, loose knitted sweaters in particular. These can be feminine without being "too" feminine--my partner is nonbinary and loves knitted sweaters for their feminine-but-not-overly-so look. In fact knitted items in general tend to be read fairly feminine--a black or grey shirt with a knitted cowl or scarf is a nice subtle upgrade.

There's plenty of colors you can try without being garish and flashy--a dark purple or navy, olive green, etc. are all more colorful than black or gray but still read professional.

Also, for something that won't change your outward appearance but may feel good to you personally--have you tried wearing stockings under your pants? I always feel much more put together when I put on some nude stockings. I only intentionally wear them with dresses, but I've had times where I took off the dress and didn't want to bother taking off the stockings, so I just threw some pants on top--wasn't uncomfortable. It might be just a bit of an internal signal to yourself that might be nice?

Also agree with changing up your shoes. Flats are nice, some boots may be more outwardly femme than you want to present, but, again, for that internal bit, many boots are easy to wear with pants over them. I have a couple of tall boots that I regularly put my pants over because I wear loose pants--no one ever realizes they're boots because they're hidden, but I know, and I like these boots, so they make me feel better. Maybe there'd be a similar effect for you?
posted by brook horse at 10:47 AM on October 9, 2018 [1 favorite]

My coworker started small steps by doing neutral or clear nail polish, and it really worked for them.
posted by corb at 10:48 AM on October 9, 2018 [15 favorites]

I also found a fantastic trans friendly tailor in Minneapolis to nip in a bit of a waist into my suit fit. So I can wear them traditionally or wear them with a silk shell or other non-collared shirt to look more like a pant suit.
posted by advicepig at 10:49 AM on October 9, 2018


Clear nail polish is an easy one, and a lot of people in your situation find it makes them feel better even if it isn't really visible. Keeping your nails better groomed in general will pretty your hands up a bit. If you want to go out on a limb, consider a French manicure, which is less noticeable than color on nails. I find my hands strongly affect my own perception of my gender, even if they aren't super salient to others, because unlike my face I see them in my peripheral vision all the time.

You can almost certainly wear brown mascara without setting off any alarm bells — especially because nobody will expect it on you. Whether you can do black mascara deniably will depend on your complexion. Seconding tinted lip balm. There's other low-key facial makeup you can do without people noticing too, but I'm not the right one to give advice on it because I barely wear any myself.

You don't mention facial hair. If you have a beard, you can shave it off. If you normally wear a bit of stubble, shave closer.

Shaving legs and armpits won't change your appearance but might help you feel better about things.
posted by nebulawindphone at 10:49 AM on October 9, 2018 [5 favorites]

I don't wear perfume or cologne, but switching to a hand lotion and soap that has a nice fragrance is also a boost for me. This lotion is J. R. Watkins Lavendar. The main soap at home also smells feminine.
posted by advicepig at 10:53 AM on October 9, 2018 [3 favorites]

I have a similar suggestion to brook horse: If you're not doing it already, shave your legs! As a cis-het woman, I put off shaving for long periods of time because it feels like such a chore. But when I DO it, it feels incredible. I instantly feel more feminine and sexy, and putting any sort of clothing on over them feels amazing.

Also, if you're not ready to wear heels, wearing a pair of wooden-soled shoes that click like heels might have a similar effect. I don't wear heels, but I love my pointy-toed clicky loafers!
posted by a.steele at 10:56 AM on October 9, 2018 [7 favorites]

Seconding the congratulations!

Things that I've noticed femme cis men doing (in more casual workplace environments than yours, but still):

Nail polish
Earrings (clip-ons are definitely an option if you're not committed to a piercing yet)
Scarves (in your workplace, something like this, maybe?)
Carrying a tote instead of a backpack/messenger bag
posted by sevenofspades at 11:05 AM on October 9, 2018

Oh! Now that more office workers carry tablets rather than laptops, stores are carrying smaller tablet-sized shoulder bags that are genuinely ambiguous in appearance between "small men's messenger bag" and "large purse." The purse I carry most days is that kind of black leather tablet bag, and if I'd started carrying it before I transitioned I don't think anyone would have batted an eye at it. I imagine if you want to be a little more striking you can find something similar in a brighter color.
posted by nebulawindphone at 11:11 AM on October 9, 2018 [4 favorites]

Congratulations! I started at fifty, as well. Here are some of the things that I did to express myself before I could be out.
  1. As mentioned above, I shaved my legs.
  2. Started wearing a few plain silver and stainless steel rings on various fingers
  3. Bought a bracelet something like this Wearing a bracelet at all made me feel more feminine, but this was deniable.
  4. Let my hair grow out.
  5. Painted my nails. (This one was pushing it, and I stopped after a while)
  6. Got my ears pierced. I wore plain steel studs.
  7. Started wearing a necklace under my shirt.
  8. I bought glasses from the women's selection. They aren't super femme (here's a pic), but they helped.
I wrote a related post on my Tumblr, in case you're curious.
posted by Tabitha Someday at 11:27 AM on October 9, 2018 [14 favorites]

- Punch up the gray and black with jewel-toned shirts, scarves, and sweaters.
- For jewelry, consider some feminine cufflinks.
- If it's something you haven't paid attention to before, maybe a skincare regimen for glowing, prettier skin? Get that manicure and a facial, too?
- If your eyelashes aren't dark, you can have them tinted black for crisper definition. It's like mascara with less fuss, and the dye lasts for weeks. Longer, fuller eyelashes is an effect you can get with clear mascara or a nighttime DIY castor oil treatment. (Most clear mascaras can also be applied sparingly to shape/groom eyebrows.)
posted by Iris Gambol at 11:30 AM on October 9, 2018

Get your eyebrows waxed/threaded? The visible result will be very muted, but it’s a femme-feeling thing to do.

And... I’m not great at men’s clothes, so I’m not super sure of specifics, but I bet there’s something you could do with a silk scarf that would fit into deniably/ambiguously feminine. Think ascot, from the menswear end, but just pretty scarf as feminine.
posted by LizardBreath at 11:34 AM on October 9, 2018 [2 favorites]

If you don't already, start going to a salon instead of a barber, and getting some stylists' opinions/suggestions for good colors for you. A skilled stylist can advise on clothes and makeup styles/colors as well as hair, and it can be a good opportunity to practice talking about yourself differently.
posted by headnsouth at 11:36 AM on October 9, 2018

I like advicepig's suggestion of getting your suits re-tailored - I love looking at photos of Marlene Deitrich's androgynous styles for that look of masculine clothing with a feminine accent.

I know sweaters have been mentioned upthread, but I don't know what you think about cardigans? Worn undone, rather than done up.

Also, hello, I am a 6'1 muscular ciswoman, who wears everything from pink dresses to men's clothes and you can woman however you damn well please :)
posted by Vortisaur at 11:37 AM on October 9, 2018 [11 favorites]

[One comment deleted. AskMe isn't a place for chiding people, and even more so over their gender stuff. I'm giving you a day off. This is a first and last warning: be decent to your fellow Mefites or get banned.]
posted by LobsterMitten (staff) at 11:50 AM on October 9, 2018 [53 favorites]

Yes on tidying up your eyebrows around the edges, and maybe get a tinted brow gel, they're the easiest way to keep eyebrows tidy and filled in in a discreet way. Generally investigate skin care - even in the privacy of your own home, the feel of a fancy mask after a mild enzyme peel is a spoiled princess thing :) For clothing touches, you can also try fancier shoe laces - I just got some ribbon laces that make my combat boots read just-femme-enough.

(Source: 5'10" masculine-looking mostly-ciswoman who likes to play with gender presentation sometimes, but gets misgendered enough in dresses that it takes a light touch.)
posted by I claim sanctuary at 11:52 AM on October 9, 2018 [1 favorite]

A manicure and a pedicure can feel really good and make your hands and feet softer. Lotions for your hands and elbows can feel really good, too.

Fluevog shoes are really great in that they can be subtly fabulous or ostentatiously fabulous, and they fit larger sized feet like you might have. Wearing slightly fun colored shoes that are still professional can make you feel good about yourself, too.

I agree with comments upthread about accessories. Especially now that it is getting cooler. A softer scarf, hat, gloves can feel good and look good. (I think this is a theme - soft!) Maybe a soft shawl, too.
posted by jillithd at 12:02 PM on October 9, 2018 [1 favorite]

I'd suggest getting your ears pierced-- you can experiment with all different sorts of femme presentation and it's relatively discreet. Plus unless things have changed, clip ons hurt like a bitch, and we don't need to suffer to be beautiful :)
posted by kingdead at 12:06 PM on October 9, 2018 [4 favorites]

There was a similar ask on this site sometime in the last 2-3 years. Some great answers there. Sorry I’m on my phone so I can’t search it.
posted by matildaben at 12:31 PM on October 9, 2018

As it gets colder, maybe leather gloves with longer wrists?
posted by pseudostrabismus at 12:32 PM on October 9, 2018 [1 favorite]

A few simple ideas: silk (or just silky-soft) undershirts, adding softly colored button-up shirts into your rotation (lavender, light turquoise, pale coral), and (so soft) cashmere socks.

If you're interested in fragrances: Atelier Cologne. They have some soft scents which are not super feminine, but not terribly masculine either. My favorites are vanilla and orange sanguine.

nth'ing the mani/pedi suggestion! Since your toes are covered by shoes, you could be less subtle with the polish.
posted by esoterrica at 12:39 PM on October 9, 2018

I'd take a look at Jonathan Van Ness on Instagram and at his outfits, generally. He often wears high heels with masculine clothing, which may be a step too far, but his fashion is a really fascinating range of masculine and feminine influences.
posted by mercredi at 12:42 PM on October 9, 2018 [4 favorites]

Plus unless things have changed, clip ons hurt

Earrings with spring-loaded or magnet-back closures don't pinch like older clip-ons. Hoops works best for the former, tiny studs work best for the latter.

(LobsterMitten xoxoxo)
posted by Iris Gambol at 12:47 PM on October 9, 2018 [3 favorites]

Get a facial, moisturize. Get your eyebrows done; I don't like them overplucked on anybody, but a nice eyebrow line presents feminine. Get your nails buffed and keep your hands moisturized, pedicure, too.

Wear a larger and more colorful muffler. Wear a scarf. If you call it a manket, I will find you and we will have a serious chat, but I like the big wool shawl. Saw a very attractive young guy the other day with a Russian style flowered scarf wrapped around his neck. Silk. Scarf, shirt more, more. There's a type of silk that is non-shiny and it is ridiculously luxurious and sexy on the skin.

I love to see a man wearing a cashmere v-neck with or without a tshirt underneath; it's not so much feminine as sensual, but use color.

Soft loafers, soft narrow shoes. Silk or no socks.

I'm sure you can find silk boxers or other underwear.
posted by theora55 at 12:47 PM on October 9, 2018 [1 favorite]

Grooming habits can go a long way. In addition to brow grooming and shaping, getting your hair cut into a more feminine style and adding highlights/color could look great. Also, working on your skincare regimen when it comes to face and hands. Using the right products will make your skin look more bright and dewy. A number of men I know also wear BB cream, which is a light, tinted moisturizer that also has SPF in it. A touch of a shinier lip balm is also a good look and will keep your lips looking very pretty. Fresh makes some that are emollient and have shine and some also with light tint that doesn't look glittery. A store like Sephora is a great help in finding the right skincare, BB cream, and lip balms. They'll even make samples for you of things that could work so that you can try them in your daily life before buying.

For next level femme grooming that could be fun, you could look into eyelash extensions. They're a bit of an effort to take care of if you want them to last, but they can make your eyelashes look amazing without makeup or false lashes. They can last about 6-8 weeks. Regular mani/pedi is also a great idea. Shaped, tidy fingernails and cuticles look great. Same for feet. If you don't want to do a lot of polishing of your fingernails, you can also buff them to quite a shine. It's a bit old fashioned, but makes your nails look really pink and shiny. Maybe consider toenail polish in a bolder color?

I agree with the suggestions to get your ears pierced. Go to a reputable piercing studio and get both sides done. Don't let someone with a piercing gun at a mall kiosk do it. My husband, who is a tad larger than you, wore heavy 1" hoops in both ears for years. It looked really beautiful. Rings, bracelets (beaded ones are getting more popular across gender lines), and necklaces are also a great way to add some feminine style.

This is a great season for accessorizing as well! Swap your winter scarf for a pashmina-style scarf in a buttery light yellow or lavender or pink. You could also find a nice shoulder bag to add to your look. Socks with flowery designs in feminine colors are also fun and offer an occasional glimpse when you cross your legs.

For non-suit days, slim fit pants with unstructured, knitwear tops is a good look. Knit blazers also read as more femme.
posted by quince at 12:51 PM on October 9, 2018 [1 favorite]

Something I haven't seen mentioned above are belts. You can definitely find something a bit more fancy or decorated. If you're feeling a bit shy about it, you can have it on under a longer top so it won't be visible at all times but you'll know it's there. Can also use a scarf or ribbon, too.
posted by acidnova at 1:02 PM on October 9, 2018

I second the idea of putting clear polish on your fingernails. Also, you could consider getting a pedicure with a pretty color on your toes instead of just clear -- something like Essie in Ballet Slippers or OPI in Bubble Bath, both of which every nail salon carries. I usually wear something very sheer in the fall and winter anyway because my toes are stuffed into closed-toe shoes, but I like looking down when I'm barefoot and seeing nice feet and colored toes.
posted by holborne at 1:07 PM on October 9, 2018 [1 favorite]

A scarf did a lot for Quentin Crisp.
posted by Smearcase at 1:27 PM on October 9, 2018 [1 favorite]

Stockings or panty hose offer good bang for the buck. Panty hose, especially, are hidden by pants and socks but feel smooth and silky against one's skin. Combined with shaving the legs, the sensation can be striking.
posted by irisclara at 1:31 PM on October 9, 2018

I point you to the Netflix reboot of Queer Eye, specifically to have a look at what Jonathan Van Ness wears.
posted by acridrabbit at 2:04 PM on October 9, 2018

Maybe pierced ears? You could alternate between more femme earrings, and more masculine hoops or studs, as the occasion calls for it.
posted by spinifex23 at 2:30 PM on October 9, 2018

I see that you already got the suggestion for pierced ears, sorry.

Do you wear a watch? Or some sort of FitBit wrist device? There can be more feminine watch styles/bands that can be acquired. With something like a FitBit, you could have a couple of different bands, and swap them out. For a more feminine style of FitBit, maybe pick a suede or cloth band, instead of the default rubber one that comes with the device.

Some of these are in lovely, feminine colors, for example: https://www.fitbit.com/designer-collections/ph5
posted by spinifex23 at 3:44 PM on October 9, 2018 [1 favorite]

Eyebrows! Eyebrows are something that seem small but are actually huge. Even with no other facial changes, groomed and thinned eyebrows can completely change your outlook.

Manicures and jewelry as mentioned above.

If you don't already use a facial moisturizer on a daily basis, that's another small thing with a big impact. Shiny lip balm is also good.
posted by The Underpants Monster at 3:50 PM on October 9, 2018 [2 favorites]

If you want to add more colors to your wardrobe without being too "colorful", I'd suggest jewel tones - eggplant, teal, burgundy etc.

Also, paint your toenails a pretty color.

I'm a cis woman, but I go through phases of wanting to run away from anything feminine-feeling, so this is kind of coming from the opposite perspective of subtle things I try to avoid during those moods:

-any nail polish, including clear (also, the act of painting your nails or getting a manicure feels very...prettifying)

-sleek or tall boots, or even pretty much any shoes that aren't lace-up. (Relatedly, a subtle thing many women do but not as many men is avoid socks altogether. Best pulled off with slip-on shoes and/or cropped pants. Alternatively, patterned socks are somewhat trendy and a pretty pattern might work for you.)

-any watch that isn't chunky

-jewelry, especially if it's dainty or sparkly

-silk shirts (sidenote: silk men's dress shirts could read as very traditionally masculine with a suit but feel very soft and feminine to you. So much more feminine-feeling than starched shirts.)

-any scarves that aren't thick and wooly

-three-quarter sleeve shirts

-anything with a pretty pattern (think subtle florals etc.)

-anything that nips in at the waist, especially coats/cardigans that wrap around and tie at the waist. (I think a thigh- or knee-length trench coat that ties at the waist could be a great addition to your wardrobe)
posted by ersatzhuman at 8:15 PM on October 9, 2018 [2 favorites]

On colors:

I see that they have been mentioned, but jewel tones are your friends. They look lovely on nearly everybody and always work with grey and black, and don't give off a pink polo frat douche vibe at all.

To start very subtly, look for something in a deep rich indigo instead of a duller navy - this will make your skin tone look more lively without being remotely risky in terms of color and will likely be available in men's clothing (which you can get tailored later if you're ready for that.) Even a dark wash indigo jean will read more femme than a stone wash.

Right now I'm seeing a lot of things in dark deep greens, which is seasonally appropriate and also lends itself to incorporating floral and botanical accessories later on. An emerald green cardigan with a shawl collar can read both "bookish professor" as well as "sweater lesbian" (in my mind they are the same person of course.)

Purple is amazing on everyone and often reads more masculine than you might think. It also mixes extremely well with greys for a luxurious impression without being too flashy about it, or with browns to feel kind of earth witchy without being a Stevie Nicks cosplayer.

Burgundy generally feels pretty masculine to me, but if you're going from no colors at all to little bits here and there this is a great color that is often pretty seasonless - meaning accessories often come in it. Especially leather goods, like boots and belts and stuff, come in some version of burgundy (like an oxblood). It can read a little goth if you're doing mostly blacks with some burgundy pops, but at this point that is a very established femme style that you might like to tap into.

I would avoid for now a hot magenta and that lovely pumpkin orange because magenta teeters a little close to frat boy and pumpkin doesn't work well with blacks and greys unless you're really into halloween. But otherwise, any saturated darker color should mix well into your current wardrobe. Think about squishy cardigans, trousers in subtle patterned suiting fabric, shirts with contrasting pops at the sleeve and collar, colorful leather belts and fun socks.
posted by Mizu at 9:26 PM on October 9, 2018 [3 favorites]

Oh, fun socks:

Sock Dreams (an old internet standard, everything you could want with incredible customer service and lots of ambiguous gender stuff in their product photography)
Ozone Socks - expensive but worth it, tons of fun and/or beautiful patterns.
posted by Mizu at 9:32 PM on October 9, 2018 [2 favorites]

Here's a previously that might have some helpful answers as well.
posted by ITheCosmos at 5:21 AM on October 10, 2018

+1000 to neatening up your eyebrows and filling in gaps with eyebrow pencil. It's unbelievable how big a difference this makes in your appearance. You could also wear a lipstick that is a good match for your lips, I like glossier's. A colleague in the early stages of her late in life transition also pierced both ears and had her daughter paint her nails.
posted by potrzebie at 7:41 PM on October 10, 2018

« Older ISO double garment rack   |   Where should I go on my way to Lanzerote? Newer »

You are not logged in, either login or create an account to post comments