How to start dressing for your gender expression

Experimenting with a new style is hard, especially if that style is gender-nonconforming or pushes society’s narrow limits of gender. Finding a look that suits you and your gender expression can be even more challenging if you’re closeted, newly coming out or just naturally anxious. But never fear! These six steps can help you figure out how to express a style that’s truly you.

1. If you’re starting from scratch, start at home.

Go through your clothes and focus on the extremes: the ones you love and the ones you hate. Some things you feel strongly about will be pretty obvious: maybe avoiding commonly binaried items, like dresses or button-ups. But other distinctions are a little more subtle.

Photo by  Dmitriy Ilkevich  on Unsplash

Photo by Dmitriy Ilkevich on Unsplash

Are your favorite jeans your favorite because they’ve come to fit your figure or because they were tighter in the hips to begin with? Focus more on style and cut rather than patterns and shades — you’ll be able to find all sorts of colors in any part of the store.

The most important thing is knowing what you’re looking for before heading into a section of a store that may be unfamiliar.

2. Start small.

Whether you’re interested in expressing a more feminine, masculine or gender-neutral identity, you don’t want to spend too much money on clothes that don’t make you comfortable. So, start off at a thrift store or cheaper spot like Ross, Marshalls or T.J. Maxx and look around.

You don’t even have to try anything on; feel free to browse around at a few different locations to get comfortable checking out a section you may not have grown up shopping in. Maybe find a couple basics to work into your routine and grow from there.

3. Plan your locations.

While you’re browsing, see if there’s anyone on duty checking clothes at the changing room. This way, you’ll be mentally prepared for any probing questions about gender expression and the garments if you still want to try something on.

For this, thrift stores are especially safe because they rarely have employees counting clothes at the changing rooms, and the changing rooms themselves are unlikely to be defined by gender.

Photo by  Becca McHaffie  on Unsplash

Photo by Becca McHaffie on Unsplash

Otherwise, check company websites for trans and gender-friendly changing room policies before heading out. Target is a great example of a store that still upholds its inclusive policy regardless of the backlash it has received.

4. Wear it around the house.

This might be a little obvious, but after you get a slew of new clothes to try out, wearing them around the house by yourself is the easiest and least stressful way to get comfortable. Try some normal activities, too — clean the kitchen, do some homework, play video games — until your new clothes feel like a normal part of your life.

That way, no matter what you wear in public, it will feel as homey as your favorite comfy T-shirt and help you feel more comfortable with the new experience of “going public.”

Photo by  Michael Weir  on Unsplash

Photo by Michael Weir on Unsplash

5. Meet people you know.

If you’re nervous about going out in your new look or if you want to show it off, get your group of friends together! Hanging out with reliable people in familiar spots will help ease you into truly being yourself in public. Allyship is real!

Photo by  Manesh Chapagain  on Unsplash

Photo by Manesh Chapagain on Unsplash

Going out in clothes most people don’t expect to see you in is, of course, the scariest and most potentially dangerous part of this process. If you’re with strong, supportive friends, you can count on them to back you up and diffuse situations that could become hostile or dangerous.


6. Especially with professional clothes: practice.

Practice, practice, practice. There are a lot of specific expectations regarding professional wear and you won’t know how to navigate them until you try.


If you’re particularly anxious about, say, getting a suit tailored for the first time, try to contact someone who’s style you admire or who you really trust to see what tips they have. Or, better yet, have that friend come with you for the fitting.

Photo by  Alberto Bobbera  on Unsplash

Photo by Alberto Bobbera on Unsplash

A lot of people won’t need to go through all these preparation steps, so if you want to start by walking into a store and buying everything you can, go for it!

But don’t feel bad if you’re a little more hesitant or aren’t sure where to start. Go at whatever pace you want until you reach a place where you’re totally comfortable with your presentation. 🍒