Lucy Grey: Gendernaut

I went shopping with Dulcinea last night. We were looking for a more suitable outfit for my first public outing—and we got it! I spent about $50 on a hat, a cute scarf, two Henley shirts, and some great skinny jeans—and we got it all at Walmart. I never thought I’d say I was glad I’d gone to that circle of hell, but I’m very happy with my purchases! Pics will follow soon. Hopefully I’ll be able to pose and post pics tomorrow, if our after-work schedules and the planets line up.

Pictures and posing are nice, but I want to talk more about the experience. The last time I went shopping for femme clothes for myself, Dulcinea and I went to Target during working hours on a weekday. It wasn’t very crowded, and there was very little chance we’d ever run into somebody we knew. The two of us stuck together the entire time, and I was confident in my shopping.

Not so at this Walmart. Early evening on a Sunday afternoon, at the store closest to my old college campus means we run into at least four of my old classmates. (>.<) Luckily, they were nowhere near the women’s area when Dulcinea and I were browsing. Even still, simply knowing there were people around who knew me had me looking nervously over my shoulder the entire time.

At some point, Dulcinea left to go look at something, and I found myself alone in the women’s section, browsing without realizing she wasn’t near me. I was holding a pair of women’s (or juniors’?) skinny jeans up to my waist when I caught a puzzled male Walmart employee eyeing me, and Dulcinea was nowhere to be found. About three shades of scarlet, I hastily hung the jeans on their rack, and left in search of the Lady del Toboso.

I know it was a dead giveaway, and I know that it shouldn’t matter anyway, but it’s a nervewracking sensation, to break social mores. Especially when I could be doing it in a situation where people from my old-unrealized-life could find out. I don’t want to out myself just yet, and here I am, all by myself in the women’s section of a Walmart frequented by almost all of my college friends, obviously checking out women’s pants, trying to see if they’d look good on me.

I need Dulcinea as an excuse to be in the women’s section. She’s my shopping beard, so to speak. Without her, I look like a sore thumb. While my rational mind says that most people wouldn’t give a second thought about a person confidently shopping and going about their business, my gut is paranoid. Which kind of translates into how I shop. I actually hovered around the dressing rooms for a good while, just trying to get up the courage to approach the workers there and ask for a key to a stall. And when I finally did meekly ask to use a stall, they didn’t give me a second glance; they just pointed to stall number six and continued their conversation with their coworkers.

I got myself worked up over nothing, it turns out. But my paranoia still says, “What if they could tell you want to try on women’s clothes? They could make a big scene and kick you out for being a pervert.” It looks silly when I type it here, but sounds so much more insidious in my head. The last thing I want to do right now is make a scene and out myself. This kind of thing is something I still have no experience doing—trying clothes on. When shopping as a man, most of the time, I can go in, grab a pair of pants in my size and leave without ever trying them on—I just know they’ll fit.

This kind of experience, distressingly, is not repeated on the female side of the store. While men’s sizes are simple, and make sense (30/32 pants means you have a 30-inch waist, and an inseam of 32 inches), women’s sizes are anything but simple. Or consistent. Some of that has to do with no standards, some has to do with the sheer magnitude of differently shaped female garments, and I think some has to do with how much fun it is to try on clothes. It turns out that women’s jeans are noticeably more elastic than men’s jeans and they do a hell of a job accenting my skinny legs and giving me more of a butt. And the scarf and long sleeve shirts do a pretty good job of minimizing my manly shoulders and neck. And the hat? Well, I’m just a sucker for cute hats.

I walked out of Walmart with Dulcinea today, $50 poorer, but a head-asplodingly-cute-outfit richer. And with a story to tell about how nerve wracking it is to shop for women’s clothes, in fear of discovery by my friends. Today was a learning and practice day. Learning that I’m still nervous about this femme side of me, but also learning that confidence can get you a long way in not sticking out—if you look like you know what you’re doing, people don’t tend to bother you. I need to practice that more.

Have any of you had nerve wracking shopping experiences?