This Is What It’s Like to Shop While Trans

For many of us, a good outfit evokes confidence. It provides a level of self-esteem that gets us through the day. And for trans women, and trans people in general, clothes are an important source of affirmation and self-discovery. It's one tiny element of the trans experience with a marginal impact. Still, feminine expression through fashion can be a joyful part of the journey, according to those who've lived it.

“It wasn’t until the pandemic [that] I started navigating feelings of affirmation and how that pertained to my gender identity,” says Audrey Robey, a trans woman from Richmond, VA, who gives styling tips on TikTok. “I started taking those first steps, experimenting with makeup and more feminine clothes as well as HRT shortly after.” 

Getting dressed can also be an exciting — and sometimes intimidating — challenge during a transition. “I felt affirmed in my makeup, and I had different hair options, but clothing was something that was really new to me and a little bit scary,” says Ms. Myles, a trans woman and makeup artist from Toronto, Ontario. “I just wanted hyper-femininity and the clothes I was wearing to be armor.” 

After all, clothes are often the quickest way to signify your gender publicly. For those dealing with gender dysphoria, a feeling that arises when your gender identity does not align with your assigned sex at birth, this can lead to a process of constant self-discovery. New pronouns, new hairstyles, new gender-affirming surgery, and new names are a few methods trans individuals undergo to feel more comfortable in their skin, yearning for the psychological, elusive bliss of gender euphoria. 

Fashion can help bridge that gap. “Going into the boy's section shopping with my mom as a kid, I’d be really upset looking at everything because I couldn’t find a single thing I’d want to wear,” says Cloudy, a trans woman from California who often speaks about the trans experience on Twitter. “Now I get excited looking at things because I can actually see myself in them.” 

Of course, a new wardrobe can be pricey for anyone, especially someone who needs to rework their entire closet during a transition. As such, cheaper outlets like fast fashion brands Shein, ROMWE, and AliExpress are good gateways into understanding style, a trial run of what works and what doesn’t, alongside thrifting. “I quickly became obsessed with Shein,” says Ms. Myles. “It provided so much access to so many clothes."

It's a valuable insight that's often missing from the fast fashion conversation: Not everyone has access or the ability to try on and purchase much-needed gender-affirming clothes. “When I started buying my own clothes, I was too scared to go into the store and actually get them,” says Cloudy. “Shein was discreet and very cheap. I got rid of all my boy's clothes and then had nothing to wear, so it was like a whole new wardrobe for $150.”

Style is wholly individual and something that comes through trial and error. Some trans women prefer jeans. Others love wearing skirts. Some love heels and others covet boots. Constantly, we evolve our taste to fit what we want, and with that, we find things that work, which is why gender-affirming pieces are so varied and individual.

For many, accessories play a huge part in expressing femininity, especially jewelry. “My jewelry is a part of my identity,” says Ms. Myles. “I come from a long line of women who love their jewelry, like my mom, my nana, my sisters, and my aunts. We’re a matriarchy who loves jewelry.” 

For trans women, a beautiful necklace or a good pair of earrings can let individuality shine (literally) when clothes don't. “Accessories show off more of my personality,” says Cloudy. “When I’m meeting someone’s parents, I wear these earrings with gold hearts on them because they’re really modest, but I’m also trying to show a committed interest in a relationship.”

Despite the joys of dressing as a trans person, there are challenges, too. Finding inspiration can be difficult. While some cited ModCloth as early inspiration, others scrolled Pinterest to perfectly curate a lookbook. Trans-friendly clothing stores exist, but when only 5 percent of the population is trans, it’s hard to see yourself reflected in wider spaces.

There are tips for shopping, however, on which almost everyone agrees: Have your measurements on hand, know your body shape, and be picky about what you want. Sticking to those guidelines can help ease anxiety around gender-affirming clothes.

“I would find looks on Pinterest that I liked and experimented a lot with different prints and cuts in thrift stores,” says Audrey. “I really dedicate my understanding of styling to the concept of the silhouette. Using the different body types — like pear, apple, hourglass, banana — I was able to build a foundation for the types of clothes that would flatter me.”

Community is, of course, also a vital aspect of exploring queer identity as a trans person — fashion included. When first reconciling with my own gender dysphoria in 2018, I linked with Valerie Keaton, a trans woman located in Toronto, Ontario, who was similarly exploring their gender identity. We shared trials and tribulations coming into our own, reassuring one another that our outfits were 10/10. Yes, fashion can be important to how a trans individual feels on a specific day, but friends make the experience something warm and valuable.  

“The process was made worthwhile in getting outfits with my best friend, Olivia. We would go to all the stores together,” says Valerie. “If the fitting rooms were locked, she’d ask to get them unlocked and hold the clothes. It was so incredibly sweet of her to do that.” 

And many people I spoke to had similar experiences. “When I started transitioning, many friends of mine were asking around our theater community for any second-hand clothing people might be willing to give,” says Ms. Myles. 

While hyper-femininity may be more gender-affirming for some, others may lean into a casual fit, shedding heels and dresses to express femininity with boots and plaid button-ups. However, there’s pressure to fit a specific mold early on that can be hard to shake. As Audrey expresses in her interview, it’s important for people to know they don't need to embrace hyper femininity just to satisfy other people's perceptions. 

“Before I transitioned, my style was very tomboy streetwear girl, and then I went deep into hyper femininity,” says Ms. Myles. “I see a lot of both Black trans women and cis women feel pressured to present in hyper femininity because it does protect us in a certain way. We don’t always fit into these tight boxes of femininity, and it can be restricting.” 

“There were lots of clothes that aren't exactly my style I tried when I started off transitioning, but I’m glad I did it," explains Valerie. “It was a time of experimentation for me, and also, I wanted to prove to myself I could wear a crop top.” 

One thing we can all agree on: Fashion is a powerful tool for feeling confident. For trans individuals especially, fashion is a statement, a way home after years of feeling like a stranger in our own bodies. The clothes, shoes, and accessories we wear show one side of an uphill battle, a constant journey uncovering what trans looks like across the gender spectrum. Fashion can be political, liberating, or an act of defiance against societal expectations. 

Or it can be a way to simply look good.