Learning to dress like a lady
January 24, 2012 8:39 PM   Subscribe

Advice to help my lady friend learn to dress more like a woman?

My lady friend recently lamented how she feels largely at a loss "dressing like a woman". Outside of work she's usually in jeans and and t-shirts, the latter most often being the kind you find from Threadless or similar. She doesn't feel very comfortable in more feminine clothing largely because she admits she doesn't really feel like she knows how to dress. I'm guessing this is something she never learned as she was growing up. She wants to learn, but I think she finds it a pretty daunting task.

It's possible I'm sticking my nose where it doesn't belong, but I was hoping I could find some recommendations on how she could work on this. As a man, I know of books like the ones by Alan Flusser and blogs such as Put This On. Are there similar quality sources for women? It seems that there are a lot of bad ones out there (so many horrible magazines).

What are good sources to help her in this learning process? Are there consultants for this sort of thing (we live in the DC metro area)?

Thank you for any help.
posted by defben to Clothing, Beauty, & Fashion (25 answers total) 42 users marked this as a favorite
Things that have made my tomboy-dressing schlub self feel more like a lady:

a really good haircut.

V, boat, and scoop neck tops rather than crew neck. Threadless can provide in this area if she truly is devoted to the graphic tee.

Grownup jeans. In my case either "skinny" and form-fitting to the body or widelegged/"trouser" cut.

ballet flats.

a good cardigan rather than a denim jacket or hoodie. I prefer the v-fronts to the crew-fronts, but it doesn't much matter. Also good: a fabulous blazer.

tall boots worn with tights, a skirt, and a sweater.

proper foundation garments.

one beautiful dress that makes her feel perfect in her own skin.

I'm not sure where I stand on whether any of this is your place or not.
posted by Sara C. at 8:51 PM on January 24, 2012 [24 favorites]

If you can locate What Not to Wear episodes about folks with the same coloration and body type, they dealt with this exact sort of scenario many times.
posted by meinvt at 8:52 PM on January 24, 2012 [5 favorites]

Spend a day watching back-to-back episodes of What Not to Wear. They do a nice job of helping women dress nicely and appropriately for their age and professional while still showing off their own individual sense of style.
posted by metahawk at 9:02 PM on January 24, 2012

The Lucky Shopping Manual could be helpful.
posted by scody at 9:11 PM on January 24, 2012

It's a lot easier if she can identify a style she'd like to emulate. It can be a celebrity, a girl she knows, a model, a clothing store or designer... Dressing femininely doesn't come naturally to me -- I spent most of my early 20s in skinny jeans and Threadless tees. However, I really like the Madewell style. I try to draw inspiration from their photographs, paying attention to how their stylists build outfits and what makes things that seem "wrong" to me work.

Using a tool like Pinterest or Tumblr to collect photos that match the aesthetic she's interested in could be really helpful as well. Then she can start to build her wardrobe with items that she loves so much that she just has to wear them, without getting that icky inauthentic "I'm wearing a costume" feeling.
posted by telegraph at 9:16 PM on January 24, 2012 [4 favorites]

Sara C has tips that definitely helped me feel like I was dressing more "like a woman."

Really though, I just thought I wasn't dressing like a woman. I focused on the "girly" things I didn't do (make up, cute hair, accessories) and didn't look at the traits that make me look like a woman (body shape, walk, mannerisms). My wardrobe is not that different from my husbands, except it really is... the cut and colors and way they hang on my body aren't specifically "womanly" but they are definitely not masculine.

Since my own perception was the underlying problem for me, I'm not sure what or if you should be making any suggestions. Unless she asks.

I think watching What Not to Wear is good because it is a show I find entertaining and has lots of helpful tips on how to find clothes that fit well. Pinterest is perfect for ideas. Starting small, with one piece of clothing she likes can make the process less daunting. For me, incorporating more "feminine" pieces slowly, gave me time to adopt the newer style instead of feeling like I was playing a grown up dress up game.
posted by Swisstine at 9:20 PM on January 24, 2012 [2 favorites]

I found The Pocket Stylist useful.
posted by Iris Gambol at 9:36 PM on January 24, 2012

Boden happens to be down for routine maintenance now, but they tend to have very nice, clean items which might be good transitional pieces-- some can be girly but there are plently of the sort of things Sara C. talks about.
posted by oflinkey at 9:41 PM on January 24, 2012

Agree with what Sara said above. I'd also like to add that you can be plenty "girly" without wearing ruffles, ribbons, and skirts. If the V neck tops feel low-cut to her, keep in mind that layering can help. I think the grown up jeans and the cardigans (especially right now!) are especially good advice. In general, sweaters are a girl's friend.

Another thought: Try things on. Yes, you know you're a small/medium/large, but really, grab a style you might not have considered and go try it on in the dressing room. It's very instructive as to what cuts and colors look good on you. Even try t-shirts on. The difference between fitted and loose can be huge. ALWAYS try pants on. It's OK for some jeans to be a little on the tight side - they'll stretch as you wear them.

Actually, thinking about it, if you're trying to feminize your wardrobe, a pair of jeans that suit your body type (by which I probably mean either "curvy" or "skinny") is an important staple. To get that, you're going to need to spend some money. I'd specifically recommend perhaps trying a Gap in a slightly higher end mall. Go at a less busy time - a weekday evening or before noon on a weekend - and I've had some decent customer service. Ask someone working there if they can help you find the right jeans for your body type. A pair of Gap jeans will run you about $70. I I'm specifically mentioning Gap because they a) have several styles b) have different colors c) have a stable selection (that is, you don't need to feel pressured to buy if you aren't certain because the same pants will still be there next week) and d) have good short/tall options both in stores and e) available online if the store doesn't carry the exact combo you need.

Sorry, babbly, I know. I have a friend who is sometimes mistaken for a boy and I know it hurts her. I'm trying to think of approaches I've taken when going shopping with her.
posted by maryr at 9:45 PM on January 24, 2012 [1 favorite]

Accessories and shoes are a nice way to ease into a more feminine style, without the stresses of trying to find clothes that fit properly or putting outfits together (especially if she doesn't have much to start with). Wearing pretty earrings with a basic sweater or putting a cool scarf on with a t-shirt make me feel more put together and girly.

I also make rules for myself when I shop, to avoid ruts. Recently, this has meant not buying shirts in my standard colors or only buying t-shirt style shirts if they have something else interesting going on. This is an easier and more natural way to branch out of a jeans and graphic t-shirt rut than going out and buying a whole new wardrobe or random pieces that don't work with what you already have.
posted by MadamM at 9:49 PM on January 24, 2012 [2 favorites]

I love the fashion blogs Already Pretty and Fashion for Nerds--they're a good mix of outfit logs and advice, while being open to creativity and non-judgmental.
posted by rivenwanderer at 10:45 PM on January 24, 2012 [3 favorites]

A pedicure, gotten regurly. Like once or twice per month.

Don't ask me why. I can't get mani-pedis because I work with food. Also, my nails on my hands are super strong and when anyone but me files (or buffs!) them, they peel and break. Bad for food service.

But having my toes done? OMG. Changes everything. Once I can wear open toed shoes with confidence, my choice of daily outfits automatically changes.


I am a former (somewhat) girly girl who now is a kitchen dog-type. A friend once joked if it wasn't night club-worthy, I wouldn't buy it - so true!

I have two looks - Night Club Hostess -or- Lumber Jack in Pajamas.

Keeping my toes done elevated my game.

This is a $20 to $50 investment per month on your part, should you wish to gift a pedi, or mani-pedi to your sweetheart.

posted by jbenben at 11:06 PM on January 24, 2012 [1 favorite]

Had a female friend whose mother died when she was in her early teens whose father got her a day with a personal shopper when she turned 24. They went to several large stores and a few boutiques in Manhattan and she learned a whole lot about what looks good on her, what works and what is not so good for her.

I could be making this part up, but I sort of remember that her Aunt contacted the shopper the next day and got her to buy some of what they looked at as a gift. Or maybe she gave my friend a gift certificate?

My ex, in conjunction with UPS, mastered the art of internet shopping and returning. She would order all sorts of things she knew she would not keep and in the privacy of home would try them on and take pictures then send them back. She would keep one in ten items.
posted by AugustWest at 11:07 PM on January 24, 2012 [2 favorites]

I think that the most important part of dressing like a girl is clothing that is shaped like girls are shaped. You can look girly in jeans and a t-shirt, as long as they are cut right - shirts should have room for the boobs, and not flatten them, go in at the waist, and out at the hips. Accessories, fancy dresses, jewelry are all great second steps, but first is fit - get clothes that aren't tight in some places and loose in others, you want stuf that fits nicely everywhere
posted by 5_13_23_42_69_666 at 11:11 PM on January 24, 2012 [2 favorites]

I think much of "dressing like a woman" is creating a feminine silhouette. That means curves and long legs. A long neck looks graceful too. Jennifer Aniston is often in tees and jeans but she looks plenty feminine because of the cuts she chooses. The trick is to look at your body shape, see how it deviates from the feminine ideal and dress so that these deviations are minimised.

I would advise your friend to look at different books and websites that talk about the different body shapes, keeping in mind that she may not fall neatly into a particular shape. I myself am some odd combination of a rectangle and a pear. Over time, with trial and error, she'll learn to cobble together different tricks from diffferent body types and different sources that work for her. This book is also useful because it looks at individual body parts rather than an overall "type".

Some comments about crew-neck tees: I personally think they are the enemy because they 'flatten out' the upper body - there is no detail to emphasise the bust nor the waist. Because the neckline is high, they make necks look short. Plus, they are usually paired with low-slung straight-cut/skinny jeans that cut right over the widest part of the hips, deemphasising curves on the lower body and shortening the legs. The overall shape created is masculine.

I've found that v-necks and low-cut tank tops are better because they elongate the neck and draw attention to the bust. Scarves, draped loosely, also elongate the neck. High-waisted jeans with heels (get wedges and wide, stacked heels if your friend wants comfort) create a long-legged look. However, keep in mind that I'm small-busted, short-necked and short-legged with few curves, and this is what works for me. If your friend has a different body type, other cuts may be better. The general principle is, pay attention to how your body deviates from the ideal feminine silhouette and, when reading these how-to books and websites, look for tips on how to dress to minimise the deviations. Be patient, look at different sources, experiment by trying on different things in the fitting room (try to shop when the crowds aren't out). Good luck!
posted by michelle lightning at 11:29 PM on January 24, 2012

A good way is for her to look at different styles - and femininity is expressed in a multitude of ways - and see what she instinctively likes (I would like to dress like that) and then have her explore those items whilst keeping in mind her body shape (I can dress like this). It does require a fair bit of effort.

I am personally going from a more modcloth/puffy skirt retro look to something a bit more sophisticated - and it's difficult - the former makes me look too childlike/submissive, the latter makes me look too sexy (particularly with jeans because I have big thighs/hips).

I am finding that I need tailored things up top because I have a small stomach and no boobs, and long, floaty things on bottom, but getting it right is an endless saga.

A uniform of sorts can always be established where she has well-fitting, straightforward items (jeans/tank top) that are made more feminine by the addition of accessories (scarves/jewellery/handbag).
posted by mleigh at 11:43 PM on January 24, 2012

Note on making the task seem less daunting: Take your time, don't sweat it if you only add 1 or 2 new pieces every few months, stop for the meantime if it's not fun! I started out changing my dress style from all baggy t-shirts and bermudas/jeans at 18 and would say I only reached the point where I was pleased with my dressing at 24.
posted by michelle lightning at 11:43 PM on January 24, 2012

Hah, your friends sounds like me! Does she have another friend who's more fashion oriented than her who's willing to take her shopping? I sometimes go shopping with a friend and the deal is that I shop for her and she shops for me. (This works better if said friend is a super girly girly girl who wants more functional clothing.) We do, however, get the final say in what actually gets bought just to make sure the stuff we buy actually gets worn. I find that doing this has let me notice a lot more styles on the racks that I normally would've just passed by without a second glance. I've also learned, through trying one what I consider to be the more ridiculous looking clothes, about certain styles and colors that will never in a million years work on me.

I notice that you tagged make up too. A good make up oriented store (Sephora, the make up counters at Macy's or any other department store) will help with that a lot. They can show you what products to use, how to use them, and when to use it.

I'd also recommend doing small things like getting eyebrows and nails done. Small things go a long way!
posted by astapasta24 at 11:50 PM on January 24, 2012

Academichic is a fashion blog by a group of young, female academics. It has lots of photographs of their outfits, but there's also a stack of tutorials which unpick the aesthetics of fashion in an analytical way, which is particularly helpful to those of us who don't have an innate instinct for it. The blog is no longer active, but its archive is a treasure trove of solid, non trend-driven advice on dressing well.
posted by embrangled at 4:17 AM on January 25, 2012 [4 favorites]

What's her body type? That will dictate a lot.

I answered a similar question thusly, and stand by what I said, but want to elaborate on fit: It sounds kind of silly, but she mostly just needs to work out some silhouettes that work for her, and the rest will fall into place. As an example, check out the grid of outfits here*-- they're almost all the same tailored, narrow general shape, whether the outfit includes pants or a dress/skirt. Any real variation comes in color, print, or fabric.

Once you have a silhouette nailed down, shopping gets much easier. If she invests in some decent-quality basics (trousers, skirts, cardigans, blazers) in cuts that she can rely on and, if necessary, has them tailored to fit her perfectly, then she'll have the skeleton of a lady's wardrobe.

*I'm using J. Crew as an example because their cuts reliably work well with my petite and not-so-curvy frame, but HMMV
posted by oinopaponton at 6:23 AM on January 25, 2012

This is something I want to make more of an effort with this year. Just looking at things I've bookmarked, this old ask stood out: What can I do to become more girly and overcome my jeans/t-shirt/converse comfort zone?
posted by Z303 at 6:24 AM on January 25, 2012

I've heard that Nordstrom's has excellent consultants/personal shoppers for these sort of situations.
posted by desjardins at 7:55 AM on January 25, 2012

This takes a lot of time. I mean it in two ways: it is a transformation process that can take months or years. Also, and most surprising to this former tomboy is that it takes time everyday and week. I dye my hair. I blow dry it. I wear make up every day. I pluck my eyebrows. I paint my nails. I spend far more time shopping, yet get less each trip (but more overall).

I am still coming to terms with being pretty when no one described me as pretty before. It is odd to get much, much more male attention for something that feels "fake". I am still me whether I pluck my eyebrows or not. At the same time, it shows that I take care of myself, that I value myself.

So even if you advise your friend, expect to feel resistance.
posted by Monday at 9:38 AM on January 25, 2012 [1 favorite]

Hi! Your friend sounds like just me.

I don't know if my experience will help, so YMMV. My body type's probably more masculine than most - small boobs, no waist, big shoulders - and anything cut to fit a typically-sized woman looks terrible on me, like you just shoved an hangnail-ridden foot into a teeny tiny crystal shoe. It looks physically awkward, so I always felt awkward.

So it became to me less about 'looking' feminine and more about feeling feminine and having an awareness of my body, even if I was just bumming around. Jeans became more fitted, tops fit closer to the body and I actually attempted to accessorise (this is an on-going mission). If I need to wear a dress, the simpler the better. And it works - I still look kind of like a girly-looking dude - but at least I don't feel like I'm wearing a costume and everything feels true to my skin. You could wear the most 'feminine' things on the planet and still look awkward because you don't feel feminine. It isn't a set concept - it's about finding where she sits on the spectrum.

As for this being your place or not: I'd only give my own opinion about this sort of stuff if she explicitly asks for comments, in the vein of 'defben, what do you think?' Even if she's lamenting her lack of skill in dressing like a lady to you, it doesn't necessarily mean she wants your comments or input. It could just mean she trusts you enough not to make fun of her and wanted someone to talk to. I've had male friends and relatives tell me very earnestly 'how to dress more like a girl' and every time, unsolicited opinion drove me mad. It made me think, 'well, why should I listen to you? You're a dude. You don't even know what Spanx is.' If she's not asking, the most I would say is 'It's tough. If you want, I could ask around for some books and blogs?' and let her take it from there.
posted by zennish at 11:19 AM on January 25, 2012

I think that the most important part of dressing like a girl is clothing that is shaped like girls are shaped

This is very true. I'm curvy - not in the 'euphemism for fat' sense (though I'm built for comfort rather than speed) which this term is oft confused with, but in the 'can carry small livestock in the hollow between my bust and hips' sense. And I spent many years in crew necks and jeans, until I realised that it wasn't a good look for me - I need things that are designed to fit a shape like that, and go in where I go in and go out where I go out. If the lady in question is this shape, then she may have a hard time as most high-street/mall clothing is cut for a very straight up and down figure - larger sizes just add a bit of width to the seams, whilst the bustline is cut for a B/C cup whether your dress is a size 4 or a 22. I have a lot of issues with getting jeans to fit and am reluctantly coming to the conclusion that maybe I'm just meant to be a dress/skirt person (my other problem: I'm very lazy and jeans are easy). I'm trying to edit down the clothes I have at the moment and go for a more retro-inspired look as a 50s shape seems to suit me much better than current silhouettes. I'm also trying to learn to buy one or two really great things now and again rather than buying 90% of my wardrobe in the sales and ending up with a ton of stuff I don't really like but think is a bargain.

One thing I have learned in terms of grooming, though, is that it saves a lot of time and annoyance if you work out what you have and then work with it, rather than against it. I have very straight hair that insists on parting in the middle - therefore I need a haircut that is without a fringe and gives volume without needing hours of blowdrying. I'm pale - therefore I need a foundation that matches my skin rather than trying to make it darker (nb if you aren't a 'standard' shade, drugstores won't help you - though they're getting better at matching darker tones I believe). I spent years wearing thin round lenses until I realised square, thicker glasses frames looked better. And then working out what colours and shapes suit you saves a lot of time when it comes to shopping, and makes shopping online easier, too.

I'm five ten and I have huge feet (my running shoes are, I think, a US size 13) and a bra size that doesn't actually exist in most shops, and I often feel like a clumsy oaf next to wee girls who can pretty much put any old thing on and look great. Most of the 'classics' don't suit me, I don't suit some colours (seriously, you won't believe how much women's clothing is pink, purple or black) because I am very pale, and heels are rarely my friend. A lot of the time, it makes me not want to bother, but I don't like the way I look on these days. Is your friend in this position, or are you looking at her and thinking she'd look so much better if only she'd...? This is the key to whether you should be asking this question.
posted by mippy at 4:30 PM on January 25, 2012 [1 favorite]

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