Trans Girl’s Survival Guide: 3 Essential Tips For Your First Shopping Trip

I remember the first time I went shopping for women’s clothing. I was only 21 at the time and had only come out to my friends and colleagues as a transgender woman six months prior. Still, it wasn’t until the middle of my senior year while living in an off-campus house away from my parents that I began seriously considering physically transitioning and building a new wardrobe.

One Monday, after hesitating all morning, I finally decided to go to the Sears right near my college campus. Soft rock covers of Christmas carols played over the loudspeaker as I walked into the store. Women were scattered across the clothing department, shopping for skirts and blouses. I walked past aisle after aisle, adorned in jeans, blouses, dresses, and sweaters. They looked gorgeous and I wanted so badly to try one on. But as I stood over the skinny jeans on display, I froze in place. How could I carry something like this around the store? Would other women make fun of me for holding on to women’s jeans? If I picked a pair out would I be allowed to try on clothes in the dressing room? Would security kick me out if I did? Worry after worry raced through my head, building off one another as I paced around the women’s department. My head grew dizzy as my arms remained empty. This wasn’t going to be easy, I began to realize. This wasn’t going to be easy at all.

And it wasn’t easy — but I got through it.

With that in mind, here are some tips to help your shopping experience go a bit better than mine did. 

Tip Number 1: Shop at an actual brick-and-mortar store (as opposed to online)

Transitioning isn’t just about the psychological peace of mind that trans women experience. It’s also about learning all new ways of expressing oneself in public, including through clothes. When I finally tried on my first pair of women’s jeans in a dressing room, it felt incredible. The way they fit around my hips and thighs made me feel so feminine. 

Granted, it took a few more visits to Sears until my personal style began to click, but the more time I spent trying on sweaters and jeans, the more I began to realize that shopping for women’s clothing was manageable. I could wear a pair of skinny jeans and look quite nice in the process. I could grab a red cable knit sweater and pass in public. The biggest obstacle in my way was overcoming my own fears, because there was no way my transitioning would move forward if I didn’t start publicly expressing myself the way I wanted to be seen. That’s one of the reasons why it’s so important to run out to a department store and simply start trying things on. As with cisgender women, no two trans women share identical body shapes. So, when it’s safe to do so, it is absolutely essential for a trans woman to try on clothing at a brick-and-mortar store to get a feel for her shape and size.

Tip Number 2: Try everything on 

While I was clothes shopping with a friend at Goodwill, I decided to skip going through a set of medium-sized cardigans on the rack. Most of the mediums at Sears hugged onto my belly, which made me feel too masculine for my liking, so it only made sense to take those off the table. But as I was tearing through the aisle, my cisgender female friend stopped me and said, “Clothing sizes are all different, depending on the store so if you find something you like, you should try it on.”

Back when I used to go shopping in men’s departments, tag sizes were pretty standard. A large at Dockers was a large at Sears and a medium at J.Crew was a medium at L.L. Bean. My friend made me realize that shopping for women’s clothing is all about getting a feel for an outfit’s shape on my body. That meant a lot more time inside the changing room than before.

Granted, my close friend was a cisgender woman, so she didn’t have the same experiences I did with transitioning, but she did know a lot about body shape, size conventions, pattern designs, and outfit choices. Even if cisgender women don’t fully understand transitioning, they can help trans women navigate the odds and ends of shopping retail. 

Tip Number 3: Start by buying basic items

Buying t-shirts, jeans, and cardigans first was my way letting me test the waters without swimming in the deep end too soon. Shopping for those things in the women’s department wasn’t as scary as trying to shop for dresses, skirts, bras, and leggings. Sure, women’s blouses are a bit tighter around the torso, and girls’ jeans are made to be snug around the hips and legs. But, honestly? It’s not all that different from shopping in the men’s section. Androgynous outfits are a great way to get used to the gradual changes a first-timer will be making to her wardrobe.

Did I end up getting rid of a lot of the clothes I originally bought? For sure. But in the end, I was finding out how to express myself in the way I’d always wanted to be seen and presenting myself to the world.

In the end, going out to a store and shopping in the women’s section was a chance for me to experiment with my style. Did I make poor decisions my first time out? Oh, yes. Did I end up getting rid of a lot of the clothes I originally bought? For sure. But in the end, I was finding out how to express myself in the way I’d always wanted to be seen and presenting myself to the world. Sure, I had to push myself to do things I had been scared of all my life in order to transition, but by taking these first few steps in exploring my style I was finally starting to become who I was. Now, I’ve never been happier that I did that and I hope you will be too.