You Need Help: Dressing Like a Grown Ass Trans Woman

Welcome to You Need Help! Where you’ve got a problem and yo, we solve it. Or we at least try.


Q:  So, the deal is, I’m a just-beginning-transition, lesbian-identified trans woman. And it took me a while to get there — I’m early-50s. So, what am I supposed to wear? I’ve got a pretty good person doing my hair for me, and I’m confident that they’ll get me where I belong hair-wise. But I’m kind of struggling with where to go in terms of clothing. I’m not particularly femme in presentation or inclination, but the lesbian-hipster aesthetic is not entirely age-appropriate.

Frustratingly, I’ve been sporting flannel (and other plaid) shirts, jeans, and deck shoes as a dude for years. Do I just keep that going? Or what?


Mey: First of all: Congratulations! Starting to transition, is in my opinion, the hardest part, so you’ve already done something that you should be super proud of! You’re awesome and you should feel awesome.

This is one of the top results for "Lesbian Fashion," I'm not sure if this clears things up or just makes them more confusing. via shutterstock

This is one of the top results for “Lesbian Fashion,” I’m not sure if this clears things up or just makes them more confusing. via shutterstock

Second first of all: My inclination is to say just wear whatever clothes feel comfortable. There’s no right or wrong way to dress as a trans woman. Basically, you could just keep wearing the same type of clothes you previously wore, but buy them from the women’s department instead of the men’s. You could definitely keep wearing your flannels, your plaids and your jeans and you would still be dressing as a woman. But I also know that that might not be the exact kind of help you were looking for here. So I’m also going to give some fashion advice.

A good first step is to figure out what kind of look you’re going for. Do you want to be a soccer mom? Businesswoman? Cool aunt? Tough lesbian chick? Outdoorsy type? Once you’ve figured that out, this will all get a lot easier. Maybe you can find some age-similar actresses, politicians, musicians or other famous people that you’d like to emulate. Like maybe Lea DeLaria, Wanda Sykes, Tig Notaro or Cecilia Chung.

Zackary Drucker rocking those layers like the pro she is. via zackarydrucker.com

Zackary Drucker rocking those layers like the pro she is. via zackarydrucker.com

Now for some specific advice. I think you can pretty much do no wrong when it comes to blazers. They’re not too dressy, not necessarily femme – but not necessarily butch either – and they immediately make any outfit look better and more grown up or professional. I would just avoid blazers that have shoulder pads. In fact, most layering techniques are pretty good for the not-particularly-femme-in-presentation-or-inclination trans woman looking for some good sartorial choices. Apart from blazers, I’d suggest getting some nice cardigans and either a jean jacket or leather jacket (or both!).

Have you given any thought into getting a nice suit or two (or three)? A good suit looks really dang good, it’s age-appropriate for whatever age you are and it’s versatile. Autostraddle has published quite a few guides to buying a great suit. And if you have the budget, you can get it tailored to fit your body specifically, which is always great. Or, for a cheaper option, you can check out Lane Bryant.

A great pair of boots is also a great way to go. It’s easy to find them in all sorts of sizes, they’re often pretty androgynous and they can help mark you as a lesbian. Plus they’re just dang practical. I also think that oxfords are a great looking pair of shoes that don’t have to seem super femme.

Reina Gossett (second from right) looking amazing in a denim button up. via srlp.org

Reina Gossett (second from right) looking amazing in a denim button up. via srlp.org

There are plenty of not-too-femme fabrics and patterns that you could look for when looking for tops that would still definitely read as stylish and sophisticated, but hopefully wouldn’t make you feel like you were overdressing or femming it up just because that’s often what’s expected of a trans woman. You could go for denim or cotton button up shirts, houndstooth or gingham – I’m a huge fan of gingham – or flannel. I mean, if you already wear flannel, why not continue? There are definitely plenty of ways to make flannel age-appropriate. Modcloth sells a lot of clothes that fit into these categories and look really great. I already mentioned layering, and here again, using flannel as one of your layers, perhaps under a blazer, leather jacket or down vest is a great look. Also, I mean, Autostraddle does have some really awesome t-shirts and hoodies that we sell.

Ultimately, though, you’ve got to just wear what feels best. This is your time to be who you’ve always wanted to be. I mean, what’s the point in transitioning if you still can’t express yourself the way you want to? So really, it just comes down to this: You do You.

Mari: Oh, the style question. I think the “what I am supposed to wear?” problem is something that’s a pretty universal experience for trans-women, regardless of the age they transition. Mey has already hit basically ALL the broad points I wanted to make, so I’m just going to reiterate the most important one: your clothing choices are about what makes YOU comfortable. The truly magical part of transition being able to let go of the expectations people have been forcing on you for years and just be yourself!

Jennifer Finney Boylan via jenniferboylan.net

Jennifer Finney Boylan via jenniferboylan.net

I really think looking for people with a style you’d like to emulate is a good first start. I happen to think Rachel Maddow is a particularly dapper masculine-of-center woman, but you have to find what works for you. You might be more comfortable looking at some of the more prominent trans women like Christina Kahrl and Jennifer Finney Boylan, who are both generally quite well dressed. Whoever you decide to look at, take note of both their clothing (cut, color, length, material, etc), and their accessories (jewelry, handbags, belts, scarves, etc), as those all go into giving you a polished look. I’d also strongly advise finding a trusted friend and making time to go shopping, even if it’s just window-shopping. Try on lots of options in lots of different styles and find the colors, fabrics, and styles that you feel fantastic in. Being willing to try on something a little different has lead to so many accidental finds that turned out to be beloved clothing items for me.

Here are a few suggestions to get your started, based on some of things I happen to think look good and that tend to be pretty timelessly stylish:

Tops: A staple of queer women of almost any age is the button up. They’re versatile as hell, since they can be dressed with slacks and/or a jacket, or dressed down with jeans or khakis. If you’re going for the sharp-dressed look, make sure they’re well-ironed. You can also wear it over a tank-top or cami to get a different look. Polo shirts are a more casual option if you’re shooting for a preppy kind of look. For even more casual, don’t underestimate the versatility of a soft t-shirt in a flattering color. Flannel, of course, is always an option, but consider leaving it untucked and mostly unbuttoned, and pairing with a color-coordinating tank- top underneath.

Janet Mock looking great in a t-shirt and blazer. Plus, bell hooks!

Janet Mock looking great in a t-shirt and blazer. Plus, bell hooks!

Bottoms: There are a lot of options here, depending on what you tend to like. Well-fitted, taylored slacks in black and grey are very useful basics for business, dressier occasions, or just because they’re your thing. Khakis are also a versatile options. When it comes to jeans, skip the skinnies (IMO), and go for a fitted boot-cut. They’re more universally flattering and stylish on women of all ages. A few years back, Autostraddle published a pretty awesome guide to jeans.

Shoes: I’m generally reticent to promote specific brands, because I abhor label-politics, but I’m just going to go ahead and suggest you get a pair or two of Doc Martens. Yes yes, I know… it’s a stereotype for queer women, but adding boots are a great option for putting some edge on just about any outfit. What’s not awesome about boots with a dress? In addition to boots, they also make fairly stylish shoes in lots of interesting styles that range from rather feminine to totally butch. Look at maybe a pair of 8-hole boots or oxfords, or a pair of their sandals for summer. As a bonus, many of their shoes tend to run a little wide, which can make finding a comfortable of women’s shoes a lot easier when you’re cursed with wide feet. I also maintain that anyone of any age can rock Chuck Taylors.

Imogen Binnie

Imogen Binnie looks great in a scarf and so will you!

Accessories: It’s pretty much required by law that you own a piece of Pride jewelry. Well, no, not really, but it can make a really clear statement about sexual orientation. Adding a scarf can really change the look of an outfit, and has the added bonus of neck-warmth! Hansen recently wrote an awesome piece on jewelry that you might find helpful. A bold wristwatch is also a great option for completing your look.

Again, I want to stress these this is JUST a jumping off point of some things to consider. Ultimately, it’s you who has to wear the clothes, so find what makes you feel happy/comfortable/ sexy/cute/confident and rock it. Don’t let anyone shame you for your style, or force their particular notions of masculinity/femininity or what a trans woman or lesbian should look like. It’s a big queer world out there, so YOU DO YOU!


Send your questions to youneedhelp [at] autostraddle [dot] com or submit a question via the ASK link on autostraddle.tumblr.com. Please keep your questions to around, at most, 100 words. Due to the high volume of questions and feelings, not every question or feeling will be answered or published on Autostraddle. We hope you know that we love you regardless.

Mey Valdivia Rude is a bisexual Latina trans woman living in Los Angeles. She's a writer, comic consultant and a trans activist. She's a bruja, a femme, a pop princess and she loves comic books, witches, dinosaurs and crying. She has a cat named Sawyer and a very successful twitter.

Mey has written 574 articles for us.

16 Comments

  1. Awesome tips, Mey. Does AS have any guides to dressing in a, for lack of a better term, “professional grunge” way (if not, future article, maybe?)? I feel as though the clothes I’m most comfortable in, the clothes that allow me to express myself, aren’t always work appropriate, and I’d love some tips for dressing in a way that conveys some of the edge I’m going for while also looking professional. Walking into Banana Republic just corrodes my soul…

    • Try a search on “Kate Lanphear” and enjoy the feast of images. Some of what she wears won’t fly in more conservative professions, but I find her very inspiring as one of the starting points in my own, similar quest. (Which also relies heavily on the more refined versions of Doc Martens, btw.)

    • Thank you for giving me words to describe my current work wardrobe, I now feel less alone in my slightly offbeat fashion choices. Professional grunge is the perfect phrase for this semester’s teaching outfits (black skinny jeans, nicer but still chunky boots, button ups usually plaid that fit my body in a non-sloppy way and a cardigan).

  2. Great article ! One suggestion to add to the mix: trans women tend to be “two different sizes” in clothing made for women. You may find it better to use separates to allow you to get a good fit. This is especially true when shopping for suits. Don’t be surprised to find the that tops that fit are 2-4 sizes larger than the bottoms that fit you.

  3. Hi! I’d just like to add- my gender presentation has changed a lot in the past year or two, and it’s hard to find clothes that look the way I want to look but fit the size and shape of the body I have. What I have found really helpful, personally, is shopping at inexpensive thrift stores like Goodwill. As someone who has always been stressed out by shopping, it feels like a much lower-pressure environment to me; I’m less afraid to try new things because if I try something I’m unsure about, even if it doesn’t work out, it’s no a big lost of money or a waste of new clothes and I can just pass it on or donate it back. Also, what has personally made me feel better about my gender than all my other clothes combined was actually getting comfy underwear that match my gender. Gotta have a solid foundation. 😉 :p

  4. I worked as a personal shopper for a while which consisted mostly of selling over-priced clothes to rich white ladies who didn’t need them, but I did learn some tricks!

    Try making a vision board before you go shopping with specific pieces, outfits, and looks that inspire you. It doesn’t have to be an actual board, it could be a folder on your computer or you could just circle a bunch of pictures in magazines. You just want to get a good idea of what your style is and what kind of look you’re going for, as well as specific pieces that seem to be a recurring theme that your wardrobe may be lacking.

    Once you’ve got that figured out, you can take stock of what you already have. If you’re a jeans and flannel girl, that’s great and it sounds like you won’t need to buy too many new things. If you want to femme it up, or just infuse some more personality, you can leave the flannel open and throw on a band t-shirt. Or roll up the sleeves and throw on a simple scarf for an easy and cozy fall look.

    If you’re finding that your wardrobe does need a refresher thrift shopping is always a good place to start. Theyre’s such a mixed bag, you might find some really wonderful treasures and great deals and you won’t need to shop anywhere else.

    If you’re wanting stuff that’s more current/on trend but you don’t want to make a huge investment Ross, TJ Maxx, Marshalls, etc tend to be good options. I get a lot of shoes at those places because they run pretty cheap. And because they get a lot of the dept store leftovers they often have pretty good selections of larger women’s shoes sizes long after the smaller sizes sell out.

    If you don’t mind spending more money a lot of higher end retailers (Ann Taylor, Anthropologie, White House Black Market) offer free personal shopping consultations. It’s generally easier if you make an appointment online so you can be sure that the PS will be dedicated to helping you and not get distracted by other customers. But you can tell them what you want (building a wardrobe from scratch, new jeans, an outfit for an event) and they should be able to help you put together some options that you’ll look and feel great in. And if they’re good at their job they should be pretty receptive to concerns like your age and tastes. I imagine that working closely with a personal shopper could present some dysphoria and/or safety concerns as a trans person, and you definitely know your boundaries and limits better than me, but if working with someone like that is something you’re comfortable with it could be really helpful, because they see A LOT of different body types and know how to dress different figures and they’ll be able to help you figure out which cuts and styles will be best for you.

    Finally, have a friend who you trust on hand to give you an honest opinion on fit and style. Because having someone else to tell you you look great makes you feel ten times better. If that person is also willing to help you plan outfits and accessorize and stuff until you build up some confidence you should definitely take them up on that as well.

    If you don’t have anyone who would be good at that, or you’re not comfortable asking anyone in real life, the A-Camp/Autostraddle Femmes Facebook group is full of a bunch of femmes (myself included) who would probably love to help a fellow queer lady find her style. Even if you don’t identify as femme, I’m sure you could post pictures of outfits or styling questions in that group and get so many responses.

    • I really like your idea of the vision board. (And well, all of what you mentioned.) I think that what has led to my most successful outfits is having a definite look in mind. I found inspiration in a character/actress from a tv show, and having a sort of focus like that when I’m shopping has helped me make much better decisions than just grabbing whatever I think might be cute.

  5. Despite the many excellent suggestions in this thread (I especially like the vision board… basically the original idea behind Pinterest) there’s one issue not brought up in this thread (and I wasn’t sure from the original letter)… sizes which aren’t available in brick and mortar stores. It’s nice to say “go to Goodwill” or thrift stores, but I’ve found (as a 6′ tall woman) that thrift stores rarely have tall sized women’s garments. If you’re, say 5’8″ or less that might not be a problem, but if you’re taller than that, don’t expect to find a lot in 3D stores. Clothing chains virtually never have tall women’s clothes in their in-store inventory (although The Gap, Old Navy, J. Crew, Eddie Bauer, Top Shop, Ann Taylor, j. jill and even *ugh* JC Penny have them online). There are a couple of other online sellers like Long Tall Sally, Next and, especially, EShakti which will allow you to enter measurements into a profile and fit the garments to those numbers, are invaluable).

    The bad news… getting clothes through the Internet takes away much of the fun of shopping and it’s a pain when something gotten through the Internet just doesn’t fit or looks sucky and has to be returned (some places include free returns, others don’t). My other recommendation is to find a good tailor or alterations person and get used to bringing them stuff. Sometimes you can find, for instance, a boxy looking shirt which has a fugly fit but nice material. Take it to an alterations place (or do your own, which I mostly do) take it in a little on the sides or even the sleeves, and it can make even cheapee garments look way better, fitted and more “femme.” Think more about creatively accessorizing. Etsy is a great place to find terrific, unique accessories. And important, if possible, don’t scrimp on the shoes. A good hairstyle, some nice accessories and cool shoes (try to see what other stylish women in their 50s are wearing) can make almost any outfit look extra good.

  6. First off I’d like to echo the comment @prairieartist made on sizes – although you might even find yourself 4-6 sizes different between top and bottoms (I’m typically 10-12 in bottoms and 14-16 in tops, and sometimes the 16s still aren’t big enough – these are Aussie sizes, I think take off 4 for US).

    I started transition basically as I hit 30, so I wasn’t necessarily going for the same style as you, but was also looking to not make teenager mistakes as I went. I’d like to give another plug to Mey’s potential suggestion of wearing what you wear now, but from the ladies section – that’s how I did it to start with. I largely wore jeans and t-shirt before, so I switched to ladies cuts for both of these and kept on wearing them. Jacket wise I got a couple of blazers and a denim jacket before getting some leather jackets when I found my feet a little more.

    The really key thing this approach did for me was that it allowed me to find a comfort zone while I dealt with all the rest of the stress of the intensive part of transition, coming out at work etc, while still feeling like I was making a visible shift to women’s clothing. After sitting in that comfort zone for a while my desires around clothing started to assert themselves in a way that was easier for me to hear, I started trying dresses etc and found that I quite like wearing them (in particular I love maxi skirts and dresses). Button tops are a great option as well, I have quite a lot of those now although I’ve also been picking up more singlet/tank tops for summer lately which go with the look for the area I’m living now.

    I resisted the docs at first, but they are a good option and I recently picked up a nice ankle boot pair with a moderate heel in London. Another pair of ankle boots was my staple for quite awhile, Naturalizer is a brand (I don’t think Australian) that are more likely to have a fit for you as I think they run to larger sizes (I’m 11 US size) and a wider foot too.

    Good luck and try enjoy yourself, don’t feel you need to change too much at once – just as much as you need to change.

    • Oh! Forgot to second Mari’s recommendation of bootcut over skinny jeans. They both look and feel better on me. I feel like my ass looks amazing in them, and anything that does that is worth it as most things do not.

  7. So, shortly after this went up, a Trusted Friend messaged me to say, “Awesome!! I thought of you when i read it 🙂 [You, another Trusted Friend and I] should set a shopping date.” So we did. And now we have an extra helping of great tips to take along with us!

  8. Yeah, you know, and there’s a few of us moving on from one-dimensional lezzy presentations, back to men’s clothes. Something bout a belt hugging the bottom of my ass holding loose jeans on me, those wider, looser men’s tees showing more bra than I should … something bout that tucklessness under boxers means “I’m ready to muff” to me …

  9. Two things.

    1) Re shoulder pads — I’ve bought jackets/blazers with shoulder pads the removed the shoulder pads. This was back before I got so fat, when the shoulders would be the only problem in something that otherwise fit.

    2) This may sound like plug, but it’s not — I have no connection to this company other than being a customer. If you’re cool with shopping online, check out FullBeauty dot com, and their sub-brands Roamans, Jessica London, Woman Within, and others. They’re the best online plus-size shop I’ve found. Prices are fairly reasonable, especially if you sign up for their email list where you get notices of percent-off and BOGO sales.

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