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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.
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.
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.
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!
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.
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.
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!
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