How to get started with… female fashion

So: you’ve come out (either to yourself or others) as a trans woman, and now you want to start dressing in a way that reflects who you really are. Or, you’re not yet sure who you are and want to see if dressing in a feminine way will help you understand yourself more closely. But where do you even begin?

A couple of observations

So in case you’ve tried going into Primark or H&M and similar shops and found yourself bewildered by the range of clothes available, panicking and leaving – you’re not alone. Male ‘fashion’ is essentially a fairly limited range of similar options – largely the only thing to change is the colour of your T-shirt. So if you’re making the switch over to dressing female, the array of choices on display can be overwhelming. Plus, cis girls are often similarly bewildered, they just get to do this at an earlier stage of life, so they’re going through it at the same time as their friends.

What I’m trying to say is that if you feel overwhelmed by the complex world of female dressing and you don’t know where to begin – you are not alone. Having a supportive friend or companion who knows her way around and is prepared to give you sometimes harsh advice about what does and doesn’t work for you is a good way to start off with the whole process of changing your look. Grab a wine or beer afterwards, if you drink, watch a silly movie and decompress. Shopping can be exhausting.

The other observation I wanted to make was – be prepared, when you first step out on the road of women’s fashion, to make a bunch of mistakes. There’ll be stuff you buy because it looks incredibly feminine on the hanger and that speaks to you. Or something is very much a style or fashion that you currently identify with strongly and you desperately want to look like that. And then when you get to the changing room and put it on, it looks absolutely nothing like how you imagined and emphasises all the things you want to hide. It’s upsetting, but common. Or, it emphasises all the things you want to hide but you still feel fabulous in it – but you don’t pass. Some clothes are the fashion equivalent of a takeaway – you really want it, and you enjoy it at the time, but it definitely isn’t good for you to have all the time…

The trick is to try and dress for your body where it currently is – by all means, get the fabulous, flouncy 1950s Dior New Fashion-style ball gown, but accept that this is something that you will probably only ever wear in the privacy of your own home. In the meantime, there are plenty of things you can wear that don’t immediately scream ‘high femme’ but will have a profound impact towards giving you a more feminine silhouette and getting you closer to passing – and feeling good about yourself – in the process.

So where to begin?

First up, observe how cis women around you dress. If you have a job, look at how the women in your office or workplace dress both for work and casually. Look at your friends’ pictures on social media (casually observe, I mean – don’t go on a big, creepy facebook crawl…). Think about the women you know whose style you admire or who you think look good a lot of the time, and then try to pin down what it is that they wear to look like that. As a general rule, most women tend to keep it fairly casual (one exception is my flatmate, but I’ve never learned the art of wearing dresses all the time, or spending that much time with a hair dryer).

AMAB people typically have broader shoulders and thinner hips than cis women, so what you want to do is dress to disguise that shape and create the impression of a more ‘hour glass’ figure. A simple place to start is a good, well fitting pair of feminine jeans and some blouses and tops that help disguise your shoulders and create a more feminine silhouette over the hips.

The kind of tops you want…

In preparing for this post, I did a quick browse of various online shops to illustrate what I mean – prepare for a heck-tonne of pictures incoming.

Something like this wrap top is pretty good because the way the neckline and crossbody wrap falls will give more of an impression of a waistline where it would naturally fall on a more feminine body shape:

These two tops are good because they have slightly defined waists and the sleeve shape helps to subtly disguise the shoulder shape and make them look a bit more drapey, which should minimise the appearance of your shoulders a bit and make a more female impression.

This top does a similar thing but in a slightly different way, also it’s simple but cute which means that it won’t stand it too much, but will have a subtly feminine look.

And finally, this blouse is pretty good because the material is drapey and flowy which will hopefully hide lumps and bumps in the ‘wrong’ places and create the impression of a more feminine silhouette in the right places.

But what about jeans?

For jeans, go for slim/straight leg and roll up the ankle a bit, or bootcut. Super skinny will emphasise your legs in a way that might look more masculine whereas other shapes will again create a bit more of a feminine silhouette. Try and look for styles that sit at a ‘mid’ or ‘high’ rise (on your waist) rather than on your hips, because men’s trousers are cut to sit on the hips so that will create a masculine shape even if they’re women’s jeans… To find jeans I’d suggest heading to a charity shop and trying on a few until you find some that really work for you.

Again, more pictures of jeans in-coming to give you an idea of what bootcut and straight leg mean – learning the terminology of fashion is another joy in itself.

In terms of style this is what I mean by bootcut: 

Bootcut jeans sit quite snugly higher up on the waist, and then gently flare a little out on the calves, as if they were widening to accommodate cowboy boots (hence the name). They can be very feminine because they sit really nicely on the butt and then flatter the legs lower down.

These, in contrast, are straight-leg jeans:

Straight leg jeans do pretty much exactly what they say on the tin – they sit medium-high on the waist and then go straight down your leg to your ankles. Sorted. These are more flattering (and therefore more feminising) than super skinny jeans because they are more forgiving. People assigned male at birth have flatter bums and narrower hips than people assigned female, so super skinny jeans really emphasise this – if you haven’t got the #booty of your dreams yet, then straight leg jeans will work wonders compared to skinny.

Dresses and skirts and flounces, oh my!

Another thing I’d recommend as it helps disguise the fact that a male body shape tends to have less on the hip, is A-line skirts. A-line is a style that sits in on the waist and comes out in an ‘A’ shape over the hips so it creates a really good impression of a naturally feminine waist – like this one here.

I would also recommend a wrap-over style dress, especially one with cap sleeves like this:

Wrap dresses are great because the tie over creates more of the impression of a feminine figure. Wear a camisole (vest with thin straps) underneath so that you make sure it’s not too low cut, but the neckline and tie at the waist do wonders I think.

What about work?

For work, if you’re in an office environment and are comfortable presenting female there, look for trousers that are bootcut and dark, and then pair them with feminine tops as above. Take a bit of time to look at what other women around you are wearing, especially people you think look good, and then think what you can bring from them into your wardrobe.

How about shoes?

On the shoe front, ballet pumps are a good option, or slightly more neutral shoes like women’s vans or Toms shoes – get them in pretty prints and fabrics so they are definitely femme, but don’t go for heels, especially if you’re tall. Walking in heels well takes a lot of practice and not walking well in them is not a great look, regardless of whether you’re trans or cis. If you’re not walking in them well, people will notice that, rather than whatever else you’re wearing or doing with your look.

Where to get clothes?

In terms of places to go to avoid spending money you don’t necessarily have, on clothes that within a few years you might be unlikely to wear much, charity shops, charity shops, charity shops are the way forward. Be prepared for a lot of trial and error, and take your time to figure it out. Once you have an idea of a few things that work for you, spend a bit more money in non-charity shops on things in a similar style and you can start to build up your wardrobe gradually.

Don’t go all in at once and try and get All The Clothes because in a couple of years you might regret those choices and looks, but you kinda have to slog through that phase a bit to come out the other side.

Wrapping it up

So this was a bit of a whistle-stop tour through how to start dressing in clothes appropriate for your gender. As you progress in your transition and start to feel more confident, you can branch out, try new things and figure out your style more precisely. When you’re just starting, honestly, you aren’t going to pass straight out of the box, but you can definitely dress in a way that makes you look and feel better while your body catches up via the slow, tedious route of HRT.

A lot of this stuff, though, does very much require honest feedback from trusted friends or allies who are prepared to give you the harsh truth about how you look from time to time. If you aren’t sure you have people in your life who will feel comfortable doing that with you, feel free to contact me for more specific advice and guidance about your situation.

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