LIFE

I Swapped My Dresses For Menswear For A Week And Here’s How It Made Me Feel

by Kim Wong-Shing

I consider myself a feminine woman. I have long hair, my nails are always painted, and when it’s warm outside, I can usually be found wearing either a dress or a crop top and shorts. For reference, here’s me on a regular day:

I’ve never been a tomboy. If anything, my personal style has only gotten more feminine over the years as I’ve learned how to embrace my body, becoming comfortable flaunting it via colorful dresses and bold makeup. These types of outfits make me feel most like me. But I think it’s important to occasionally challenge yourself to stretch beyond your personal boundaries, and I can’t think of anything that’s more of a stretch for me than menswear. I’ve never shopped for it, never worn it, never really even imagined myself wearing it.

Still, plenty of women swear by menswear. They say it’s more comfortable, cheaper, and sturdier than clothes designed for women. (And let’s be real – they all look so dang cool in it.) So a few weeks ago, I put myself to a difficult test: For seven whole days, I’d wear outfits consisting entirely of menswear. I was curious to see what it would be like. Would people treat me differently? Would it be hard to dress myself? Would I feel like a totally different person?

As it turns out: Yes, yes, and YES.

The Prep Work

The Prep Work
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Before I could properly channel my masculine side, I had to go shopping for men’s clothes. That turned out to be the hardest part of the entire challenge because — full disclosure — I hate shopping. And making things even more difficult was the fact that menswear is not designed for people with my body shape, which is best summarized as “extremely tiny.”

So on the day I decided to get my shopping over with, I breezed right past the men’s jeans aisle. Simply put, that was not going to happen. The boy’s section started to look mighty appealing as I browsed some racks, but then again, I didn’t want to look like a little boy for an entire week. I hadn’t felt this lost since my mom forgot me in a grocery store when I was a kid.

Luckily, I had a “Masculine Clothing for Women 101” expert on hand to help me out: my girlfriend! She gave me a bunch of useful advice, like, “Joggers are the only men’s pants that will fit you,” and, “Never wear a cami with basketball shorts; it’ll look like you’re borrowing your boyfriend’s clothes.”

In the end, about a third of my new menswear wardrobe was borrowed from my girlfriend, a third was ordered online from Forever 21, and a third was stolen from an ex-boyfriend. (Thanks, Mark!)

Day 1

Day 1
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Early on in my menswear challenge, I realized that I couldn’t just aim for “dress like a dude” but instead had to pick a specific kind of dude to be. “Dapper Businessman” was definitely out because of the whole “extremely tiny” thing, so I went with “Skater Dude.” You know the type: dresses real casual, doesn’t own a bed frame, and possibly still borrows money from his mom.

For Day 1, I borrowed pants and a jacket from my girlfriend and threw on a hat. Done. (Hats go a long way in making one look less girly, and I wound up relying on them frequently over the course of the next week.)

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So how did the first day go? Well, when I went to a restaurant in this outfit, a man straight up dismissed me after I spotted him looking me up and down — no catcalling! I’d call that a win.

Day 2

Day 2
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In this photo, I’m thinking, “Ehhh, OK. Maybe I’m not appealing to creepy men, which is awesome, but do I look good? Debatable.”

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I followed my girlfriend’s advice again and stuck to men’s joggers and T-shirts for Day 2, but I had mixed feelings about the look the second time around: I felt impenetrable to the male gaze, which made me more confident than ever before, but I also had no idea how to style myself, which simultaneously made me less confident.

Choosing clothes to wear for my menswear challenge was beginning to feel like a struggle, as my outfits never really looked the way that I thought they would. It was like being 15 and awkwardly learning how to dress my body all over again.

Day 3

Day 3
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On Day 3, I ran into the aforementioned ex-boyfriend, Mark (hey, Mark!), with whom I am still friends. I don’t think he’s ever seen me dressed in boy clothes before, but if he noticed the difference, he certainly didn’t act like it. And to be fair to him, everything about me is so feminine that, although I was technically dressed in full menswear, I didn’t look all that masculine. I’ll probably always be read as a woman no matter what I wear.

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But in my head? Oh man, I felt so masculine in this outfit. Honestly: The more I wore men’s clothes, the more I felt my brain shifting to a more “masculine” mindset. I felt the urge to take more initiative, to be more assertive, and to be more protective of my lady friends. I also felt more at home among dudes. (All this from a pair of joggers?!)

Day 4

Day 4
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These pants are from the men’s section of Forever 21, and they are not joggers. Amazing.

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By this point in the challenge, I was starting to feel comfortable in my dude clothes. I really loved the contrast between my feminine physique and my boyish outfits, in large part because it announced my queerness to the world in a way I’d never tried before. It was the first time I’d stepped outside of that “masculine versus feminine” box in a visible, public way, and I was surprised to find it so freeing. It forced me to own my queerness more than ever.

Day 5

Day 5
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Social experiment moment: I wore this outfit to go out on the weekend. I met a musician guy at an open studio, and we chatted and exchanged Instagrams. He didn’t hit on me at all — that is, until he saw my Instagram, which features pictures of me dressed in feminine clothing. “Oh, wow!” he told me upon scrolling through my account, seemingly shocked.

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Still, it didn’t shake me. “Swagger” is a word that is usually associated with manliness, not femininity, and I felt like I finally had it.

Day 6

Day 6
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Again, I managed to scramble together an outfit that I felt good about. (FYI: Those are boy’s basketball shorts, but who cares? They fit.)

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I wore this bright soccer jersey all day, which prompted one woman to ask me about the World Cup and another woman to ask me which country’s jersey I was wearing. I was (hilariously and utterly) clueless both times. Didn’t they know that I was basically wearing a costume?

Day 7

Day 7
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This is the face of someone who was VERY RELIEVED to be going back to her regularly scheduled programming soon. Wearing menswear for the week made me feel much more powerful and ~swaggy~ than I imagined it would, but it also felt like a vacation from my regular life as a femme woman — a vacation to a place that was amazing and fulfilling and inspiring, but also so, so foreign. I was ready to go back home.

Plus, as you can see, I was running out of T-shirts.

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The next day, I returned to one of my standard feminine outfits — crop top, short shorts, oversized jacket. I made it just two blocks from my apartment before I was catcalled for the first time in a week. Coincidence? Maybe not.

I’ll always relish my femininity, but as difficult as this week was, I’m incredibly glad that I followed through with my decision to step out of my comfort zone. Wearing menswear felt like donning an armor of sorts, and it put my brain into a completely different mode of confidence. I’m excited to incorporate some of my dude clothes into my everyday wear. Joggers forever!