Real Life Shopping Adventures Of A Transgender Teenager

Real Life Shopping Adventures Of A Transgender Teenager

It was immediately clear that Beverly was not expecting a voice as deep as mine to respond from behind the fitting room curtain as she pleasantly strolled by and asked in her delightful British accent, “Are you ladies doing okay in there?” Her fellow employee had been the one to set me up to try on my finds and so her startled “Excuse me?” was less out of judgement and more out of the simple complete lack of having expected it. Hearing this in her voice, I muttered “no worries, I’m just transgender, it’s confusing,” to the giggles of my friend in the neighboring booth and went on trying on the awesome peacock skirt that I ended up buying.

It wasn’t always so easy. At 32, completely out and living openly as a transgender person, my experiences with shopping are vastly different from that of a mid-teen me, who would’ve been far too terrified at the idea of anyone jumping from shock at my voice to ever reply in the first place. Even the idea of walking into a store, being seen as a teenage boy perusing the women’s clothing, taking something I liked and actually asking to try it on seemed so daunting, so unachievable a task that you may as well have asked me to go ahead and master calculus and whip up a cure for cancer using household goods while I was at it. As an outlier, an “other,” someone falling well outside the imagined customer base for the clothes I wanted, I always imagined the scenarios running through sales clerks’ heads, the judgement and suspicion. I imagined I’d incite the same type of nervousness that I’d had when working in a home improvement store and the somewhat menacing man with an Eastern European accent asked simply where could find “Duct tape… and rope.”

I developed a complicated system of work-arounds, excuses, and vague explanations all to accomplish the task of giving money to someone who should be glad to take. I tested the waters and slowly became more and more confident in my schemes. They wouldn’t see through my fool-proof plans! I wasn’t a deviant, I was just buying a nice pleated skirt for my girlfriend as a present, because that’s what teenage boys do, right? They go alone to Target and pick out whatever skirt looks like it might fit, hurriedly make for the register and get the heck out of there, as a sweet gesture for their girlfriends. And on those rare occasions in thrift stores when I resigned myself that I had to try something on to make sure it fit, I was totally convincing in my explanation that I had a costume party to attend… in July.

Of course there were stumbles. There was the grey-haired fitting room attendant who responded to my “costume party” with a deadpan “Sure,” before eventually unlocking the fitting room for me anyway. I think she was on to me. An sales girl at Victoria’s Secret relentlessly tried to earn her stripes as an expert upseller by pressing me to buy a matching bra for the briefs I had picked out. “She’ll love a matching set, trust me, it’ll be worth it,” she pushed. I of course couldn’t just tell her, “Look I don’t want the bra because I can’t discreetly wear it under my clothes like these Second Skin Satin briefs, alright?!”

But, of course, I actually could. And that’s what eventually happened. A few years before I came out publicly, the aspect of constantly lying, of pretending to be someone else just to buy clothes became exhausting. I was tired of deciding on someone’s behalf that who I was, was an issue. And so one by one I let my fictions go. It turned out I rarely needed explanations. If I simply said, “Hey, I need a fitting room,” one was provided. I could ask for help finding that skirt I saw online. I could ask for suggestions even and usually get them. Once I let my guard down, shopping openly created a place where I could absolutely be myself and if anyone had a problem with it, it was literally their loss because my dollars went somewhere else instead.

It’s not always perfect, there’s the awkward responses, the “Excuse me’s” from people not expecting it, but in a way, each of those tiny coming outs over the next few years gave me the training I needed for the big one that would follow. When I enter a clothing store now, there’s rarely any doubt just who I’m shopping for. And on the occasions when the clerk still does ask “Well what kind of stuff does she like?” I can triumphantly state, “Well, ‘she’ is me, and I like this.”

Rye Silverman is a writer and comedian based in Los Angeles. Rye has been seen on the Fusion channel, is a contributor to the Huffington Post and runs a blog about style, pop culture, and gender called Chick Like Me.


Rye Silverman is a writer and comedian based in Los Angeles who has been seen on the Fusion channel and in the Women in Comedy Festival. Rye has also been a contributor to the Huffington Post and runs a blog about style, pop culture, and gender called Chick Like Me.

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