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6 Things I’ve Learned as a Dude in a Dress

My original title for this piece was “6 Things I’ve Learned from Wearing ‘Women’s’ Clothing,” but the concept of “women’s clothing” really bugs me. As Eddie Izzard has often put it, “They’re not ‘women’s dresses.’ They’re my dresses. I buy them. It’s like when women wear trousers. They’re not cross-dressing, they’re not wearing men’s trousers.” The fact that we segregate our clothing stores by gender, rather than article of clothing mystifies and irritates me. Put the Disney Princess nighties on the same rack as the Pixar’s Cars ones and you free the children, just a bit, from a world of harmful expectations.

However, rather than rant about the intolerable binaries which structure our current society, I’d like to share with you a few things I’ve learned in my years as a hairy, male bodied person in a dress.

1. I Was Taking Pockets For Granted

I won’t say I wasn’t warned. I knew of the pocketless world which I was to enter by adding skirts and dresses to my wardrobe. I’d heard countless female friends bemoan their tiny, even fake, pants pockets. I’d seen the joy on their faces showing off pocket dresses. I knew of this world, but I had never lived it. As someone who always carries a wallet, mechanical pencil, pen, cell phone, Pitt ID, lighter, keys, and an assortment of change in my deep man pants pockets, the shift to having nowhere on my body for any of my accouterment, was quite shocking.

There are a handful of time-honoured methods for compensating for lack of pockets. Naturally, there’s the tuck it all between the breasts method, but, being all man-chested, that one doesn’t work for me. I mean, from time to time I can tuck some papers in there, but a phone’s gonna drop on through. And so I have joined the ranks of purse lovers! Got myself a handy side bag, plus a black velvet clutch, from Goodwill and I’ve never looked back. I know it borders on blaspheme, but a cute bag on my side might actually be better than pockets! (My friend Sam points out that the whole no pockets thing is actually a giant con from the fashion industry. Quote: “If we don’t give them pockets they must buy purses, muahaha!”)

Lesson Learned: Pockets on femme clothes are a total scam and rip off, but purses are a surprisingly fun alternative.

2. Doesn’t Matter if You Have Boobs; Catcalls are for Everyone!

Nothing makes me feel quite like I’ve crossed the line into how women live than when I’m out in club clothes and guys catcall me. Catcalls, the unsolicited, flirtatious comments from people on the street, are one of those often attacked behaviors associated with “rape culture.” In general, I’m very against them. They’re usually aggressive and are often accompanied with following people, and beyond that simply make many people feel sexualized, uncomfortable, and deterred from trying to spend the night looking pretty out and about.

For myself, however, I love catcalls. Maybe it’s because I get to choose, to an extent, when I’ll get them. I know exactly what to wear and which porches I need to walk past in order to get a “Shake it!” or a wolf whistle thrown at me. Who’s to say whether they’re mocking the dude in the dress or honestly coming on to me like they did the chicks walking by three minutes ago? Either way, it’s an odd little ego boost to know I can get harassed just like the women. And, hey, at least I know “Nice legs!” is from the heart…

Lesson Learned: Catcalls can be really uncomfortable, but, damn, they can make me feel sexy.

3. People Believe They Have a Right to Tell You What to Wear

One of the most interesting reactions to being the dude in a dress is when you’re the dude in the dress not in a dress. A sizable demographic of people who’ve met me first while I was wearing femme things come up to me on more masculine days and ask me “Where’s your dress today?” Now, while I’m tempted to retort, “On your Mother’s floor, must have forgotten it last night,” I usually laugh it off with a “Where’s mine? Where’s yours?” 

Often these are the same individuals who, when I met them, asked “Why are you wearing a dress?” Both questions are indicative of a wider issue. Our society seems to come equipped with an entitlement to be over-concerned and policing regarding the clothing of others. Heck, wear a suit for fun one day and everyone wants to know what you’re all dressed up for. Watch Seen at Pitt during the winter and every day you’ll see a new guy being chided for wearing shorts in the cold (to show off his masculinity, they claim). I’m going to go ahead and spearhead the “Just Leave People Alone and Let Them Wear What Makes Them Comfortable” crusade; feel free to join in.

Lesson Learned: “Getting away” with wearing something, doesn’t mean everyone and their mother won’t stop to ask you about it.  

4. “Too Short” is Totally Subjective

Here, enjoy this “scandalous” picture of me in my shortest dress on my bike, Volare, courtesy of Maura Barker’s OverheardAtPitt Twitter post, while I give a quick rant about “shortness.”

My general rule for picking and wearing clothes is that “If I’m not showing, I’m good to get going.” Particularly, as long as I’m not hanging out for the world to see, I don’t have a problem with the length. This rule is also why I don’t wear pencil skirts or bodycons- they’re just too revealing. Hinting is not revealing. And honestly, I see gals going off to parties and even class in far shorter stuff than I wear, and no one’s scolding them for it! Unless they are, actually I do think they are; in which case, let’s refer back to #3 on this list.

Who is a short skirt hurting? You know what’s up there no matter how long it is! I like wearing them short because it lets me tap into the world of the girls who wear them short. We understand how hot or how wanton (same thing in the eyes of those who care) it makes us feel! Really forces me to keep my legs together and bend down properly. I’m not really trying to show the world what I’ve got, just get really close, for fun, you know. If my outfit is too short for you, don’t wear it! It’s obviously not too short for me!

Lesson Learned: “Too short” might be a thing in the Temple, but on the street either you’re flashing or not, and it’s your business on which side of the line you are.

5. The Joys of Taking Heels Off is Almost as Great as the Joys of Strutting Them

Anyone with big feet will know that, as the memers say, “The Struggle is Real.” I’ve got size 11 feet in Men’s which means if I’m going to find a pair of heels, they’re going to be 12 or 13 comfortably. So, when I find a pair of heels that fit and look good, I’m going to wear them every chance I get!

All evening I’m out there, stepping smoothly over sidewalk cracks, heel-toeing it past all the catcallers to the places where a girl’ll say “I’m in a sorority and you wear those better than me!” Talk about ego boosts; I’ve only been doing heels for a year, they’ve been expected to wear them their whole lives! (Maybe it’s because I have something to prove…)

But after a long night of showing the world that heels are for everyone with the guts, and calves, to wear them, I’m done. I want my feet back. I want to wiggle my toes and check if the back of my ankle is bleeding. So off they come, getting chucked into my messy pile of shoes. I come down out of the clouds a few inches to stand on all four corners of my feet. I relax as my feet pulse from all the beauty they sauntered in.

Lesson Learned: The freedom to be a dude in a short skirt and high heels is only matched by the freedom felt when the heels come off!

6. Life Hack: Deodorant Stops Chafing

Not too much to say on this one, and honestly, any dress or skirt wearer worth their hem knows the tip, but nothing prevents and soothes that inner leg abrasion than a stiff stick of deodorant! Not to say I didn’t chafe in certain shorts when I only dressed masculine, but I always ended up hiking the crotch fabric up as a barrier. If I wasn’t doing that, I was just grinning and baring it (“like any self-respecting man is supposed to” *vomit*), but when I turned to skirts and found the same problems, I had to ask how the women do it!

Lesson Learned: No more must I live like a barbarian! I’ve got deodorant to fix my rub!

So there you have it, an incredibly non-exhaustive list of the lessons I’ve learned from donning the feminine wear!


Image Credit: 1, 2, 3, 4

Benjamin Wahlberg is a Senior Psychology major, who teaches Sunday and Hebrew School, sings internationally with the Pitt Men’s Glee Club, and also writes for the Pittiful News. More of their dialogues on gender, clothing, and Queer Judaism can be found at BenInDresses.tumblr.com

-Benjamin Wahlberg is a Senior Psychology major, who teaches Sunday and Hebrew School, sings internationally with the Pitt Men’s Glee Club, and also writes for the Pittiful News. More of their dialogues on gender, clothing, and Queer Judaism can be found at BenInDresses.tumblr.com.
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