Disclaimer: This article may contain some triggering language and deals with themes of body dysmorphia, gender dysphoria, gendered language, and transition. If you aren’t ready for this, we have other articles that might suit your fancy. 

If you are a cis woman, there are a lot of things you take for granted. I’m talking about how you got dressed in the morning. So while this article can be read by anyone, this article is especially for the cis girls out there.

We are the gatekeepers of femininity and it’s time we opened the gates.

Do you remember when you were 16? And you didn’t know how to dress or what colors looked good on you? You felt awkward trying things on and unsure of yourself. Multiply that by a major order of magnitude and you might have an idea of what it’s like for transgender women trying to balance identity with femininity. 

It’s especially hard to come out when you still present as male. Trying to make that transition takes a lot of steps, but one of the more daunting is figuring out how to dress like a woman. Not only would you have to worry about looking good, but many trans women care about “passing” and “passing” is hard. 

“Passing” means not coming off as trans to the passerby. Passing is a sensitive subject in the trans community, so supporting your friend where she is most comfortable is the best move. Some trans women forgo passing altogether and go for an androgynous look, some never think about it, and for some, it’s all they think about. How ever they come to their look, it’s up to us, as cis women, to help them achieve it. It’s not always a difficult journey, but it does take a lot of practice. 

Coming out is hard enough, imagine having to do it while also learning everything we learned in our youth. You would have to do all the guesswork that comes with fashion along with the pressure of passing for some and the energy to rebel against it for others. They already have enough to contend with when it comes to stigma, so make it easier.  It’s time to help our trans sisters fight the good fight – with clothes and makeup!

Offer to Help

Many cis women are game to help but need to be asked. But even the act of asking can be difficult and it’s much easier to accept or decline an offer than it is to put together the gumption to ask. Don’t make them do the work. Offer yourself! Be the one safe enough to get them what they need.

Many trans women have a hard time shopping for the first time. Especially for underwear and bras which they will have a hard time trying. Those are usually the first things they need and many don’t know how to buy them. So applying your know-how will make a huge difference. 

Tell them about the difference in band size, and talk about preferences like underwires and bralettes. Maybe even buy the items for them first so your friend doesn’t have to worry about being male-presenting in a female environment. You can even pretend to be a girlfriend who is choosing lingerie for her partner.

Take her measurements and apply your hard-earned wisdom of sizes and colors. Show her how to use measuring charts. And most of all, encourage her! A lot of trans women are too shy to try the styles they really want and might gravitate toward more masculine styles out of comfort. They might need some extra work to get them out of their shell.

Have a conversation about triggering language

Every trans woman is different and some are a lot more sensitive than others. Saying phrases like “man in a dress” can be a horrible thing to hear. Be sure you know how to properly guide her using words she will be comfortable with. 

Most trans women have been uncomfortable in their skin for years and years, so body issues are very common. Taking the time to talk about this first will help you support her properly.

Be gentle, she likely didn’t get to have a girlhood so she may be trying out the styles she wanted now. Indulge her, advise her, and support her, but be mindful of how your words can cause more pain and confusion.

Make A Mood Board

This might seem a little surprising, but many trans women don’t even know their own taste yet. Many never got to be girls, so for those people, this is their first foray into fashion and style. Letting them explore Pinterest and figure out their #aesthetic is a great step.

You can start by showing her different style choices like “Dark Academia” or “preppy” or “punk”. See what appeals to her and then plan your pieces strategically. Is she normcore? She’ll need jeans then. Is she more vintage? Maybe reach for the twirly skirt and structured blouses. Whatever it is, there will be a way to make it work, so start with the “genre” of clothes and then find out what looks best on her.

Share your stuff

Before a trip to the mall, let her shop in your closet. Even if you aren’t the same size or shape, it will be a big help to see feminine cuts on her. You don’t have to go out, it’s just to see how the shapes look on her body. Zip as best you can just to get the idea.

While all body types are different, the bulk of trans women will have the reverse triangle shape. We will go into which clothing will be helpful later, but we’ll start with sharing your makeup.

Play dress up!

While most cis women have a long time to trial and error their way into what they want to look like, most trans girls don’t have this experience. They have to start from scratch as an adult, so help them out by letting them try on YOUR makeup. They can see what colors to start with and what might look good on them. 

Teach them how to play with makeup and show them the techniques. They will inevitably do it badly the first few times, even the first twenty times, but that’s what practice is for. Be their safe space.

The makeup counter is a scary place and there are so many choices. You can’t just try everything on your face and the back of your hand is not as helpful as most people think.

At home, she can practice. Your trans friends can determine a lot of things from playing with your makeup. She can find out if she looks good with bright colors or if she needs to stick to nudes, how to use shimmer, and which lipsticks to avoid. Let her try your techniques and do all the trial and error you got to do in your teen years.

Pro tip: putting eyeliner on people not accustomed to it will be hard for the first few tries. Have your friend kneel in front of you facing away from you, then have her look up. That should make it easier for you to apply liner without coming straight at her face.

If you don’t have the same taste or body type, let her try some things on anyway, clothes fit differently on everyone and you can find some cuts and colors that work on your friend. More on cuts later.

Go through your Pinterest mood board together and watch YouTube videos about how to dress. You don’t have to take all of their advice, but it’s a great starting point.

Remind her that different body types exist

Dysmorphia is a common and terrible symptom of being trans and it’s so hard to get over. Some trans women have very muscled bodies and don’t think they can ever look feminine. Some are naturally slim and long and worry about being too tall to be “girly”. Show her pictures of athletic women or women who have fewer curves to make it clear to your friend that even women aren’t always shaped the way women are supposed to be shaped. Yes, it’s hard AF. Welcome to being a woman!

For me, elite gymnasts, tennis players, and other athletes were helpful pegs. They have so much strength and it shows, but many don’t have the more traditionally feminine curves. They can be a great example for your insecure trans friend.

Go shopping with her

For the first few times, your friend might be too intimidated to go shopping on her own. Not only can you provide healthy feedback, but you can also keep away the nosy sales ladies. They can sometimes be a trans woman’s number one fear. So being a buffer and being there to run interference is really helpful.

Protip: Bathrooms are a huge stressor for trans women, if you are going on a trip to the mall, familiarize yourself with the PWD bathrooms or family bathrooms as they are more gender-neutral and your trans friend won’t have to worry or hold it in.

Learn how to flatter HER shape

Many trans women have the reverse triangle body shape, which means that their shoulders are broader than their hips and their torso tapers down rather than flaring at the waist. Many trans women need to create the illusion of curves. Below you will find a basic rundown of how to flatter that shape.

Protips:

• Stay away from spaghetti straps and sleeveless tops. Many of these cuts will show off her arms which, if they are muscular, could be a problem area. 
• Cardigans and shawls are your friends.
• Look for gathers around the hips. Or ruching around the waist. This will make her waist look more nipped in and can make her hips look bigger
• Flared skirts and flow-y pants are great starters. A good way to balance a silhouette with broad shoulders is to have flared bottoms.
• Stick to more solid colors on top. Save the patterns for bottoms. They tend to draw the eye and you don’t want to call as much attention to the lack of curves on top.
• ¾ sleeves are the most flattering to the reverse triangle body type. This will keep the eye on the center and draw away from less feminine-shaped hands.
• scoop necks and v-necks are some of the best ways to draw the eye away from broad shoulders
• A-line skirts are always a good idea. A-line skirts with a little bit of flare and patterns will disguise a long torso and no hips.
• High-waisted pants are a must. One of the downsides of the reverse triangle shape is the very long torso, shorten it with high-waisted pants and flared tops.

Again, every trans woman is different, so trying on clothes will be essential. Outfits are all about balance, so if she likes a certain item, don’t just say no, try and find a way to make it work. Layers can be hard in this country because of the weather, but light jackets and diaphanous shawls can be stylish ways to hide problem areas.

As cis women, we take a lot for granted. It’s easy to forget just how hard it is to figure out how to perform femininity right. We don’t have to worry about stares or anxiety over where to use the bathroom, so it’s up to us to make sure our sisters are safe. Since we have cis privilege, we must help the trans women in our lives feel like they are finally getting to be themselves. 

In the end, your trans friend may not want to look like you or even any other woman, but she does want to look good. You can be instrumental in helping make that happen.

Always remember, you are the sidekick on this journey. She is the main character. She is Cinderella. You are merely the fairy godmother. You are the Judy Greer to her Katherine Heigl. So be sure to make it all about her and be her protector. If we make ourselves into better allies, maybe a few more trans women will feel comfortable enough to come out of the closet.

Happy Coming Out Day!