I Wore Men's Clothing for a Week, and the Resulting Looks Might Surprise You

Welcome to I Tried It Month, where we’ll be publishing a new fashion, beauty, or wellness article every day that features a first-person account of shaking up an old habit, pushing beyond a comfort zone, or simply trying something new. Follow along for 31 days of storytelling, including everything from trying new beauty treatments to copying the most risqué runway looks of the season.

There’s no doubting the fact that oversize, menswear-inspired fashion is in right now. For proof, just look at every daytime look worn by Bella Hadid and Hailey Bieber, or any recent runway show for The Row, Peter Do, or even Miu Miu (its S/S 22 collection was more than just covetable micro minis and belly tops). But when I tasked myself with testing out this trend a few weeks ago, I knew I had to go all in. In other words, rather than styling womenswear that only looked like menswear, I figured it’d be more of a challenge to go straight to the source: the actual men’s department. 

And a challenge it was. Despite the fact that I’ve made a career out of shopping for womenswear, adapting to the section across the way took more trial and error than I’d originally thought. For starters, men’s sizes are entirely different from women’s, meaning that I had to measure and recalculate all of mine accordingly. In addition to that, almost everything is longer, lower, and broader, meaning that my usual styling hacks would have to likewise adjust. That being said, once I got the hang of it, putting together outfits using pieces that I’ve long ignored began to give me a fresh perspective—and lots of inspiration. 

Arguably the biggest lesson I learned from introducing men’s clothing into my wardrobe was the importance of proportions. For me, most of the pieces I tested out were on the baggier side, with pants, especially, sitting lower on my hips and being wider and slouchier in the legs. To counteract that, I tested out pairings that included cropped and fitted tops and jackets that offset the oversize nature of the look’s bottom half. 

I also wanted to create balanced ensembles that weren’t obviously pulled from the men’s department, but instead, felt in sync with the rest of my wardrobe. In turn, I spent a lot of time switching in and out flirtier pieces like corsets, heels, crop tops, and low-rise fitted trousers until I found combinations that clicked.

Ahead, find four looks from my week in men’s clothing that convinced me to shop in the menswear department more often.

As someone’s who has spent much of their adult life trying to find the perfect pair of jeans (fitted in the waist without a gap, loose in the legs, and just long enough to reach the foot of my boots without flopping over them), it felt pretty unnatural to shop for a pair that I know wasn’t designed to correctly fit my body. That being said, once I came to terms with the fact that men’s denim would sit more around my hips than my waist and not hug my body the way a women’s pair would, the baggier style started to grow on me. I ended up liking them so much that I bought multiple pairs of men’s jeans and have been wearing them constantly. What can I say? It’s nice not to be confined to denim that you have to lay on your bed to zipper shut. 

Wearing: Zara jeans; Wandler Rosa Leather Slippers ($480)

Unfortunately, the white Zara jeans that I snagged have since sold out, but this black, straight-leg alternative is equally as good.  

When I’m testing out a men’s piece, especially a jacket or coat, I like to size down one or two sizes.

A perfect example of a women’s shoe that gives off a menswear vibe.

I love the idea of going a bit against the typical winter-fashion grain, which is how this look—including lots of white after Labor Day—came to be. Since my trousers and turtleneck were both pretty fitted, this felt like the perfect occasion to go bigger with the coat and add a masculine shoe. Therefore, I opted for my favorite oversize peacoat from Nanushka’s men’s section and a pair of men’s suede loafers from Grenson. 

Wearing: Nanushka coat; Zara pants; Uniqlo socks; Grenson loafers

Introducing the updated womenswear version of my peacoat.

I could’ve paired this turtleneck with literally any of the menswear pieces I tested out.

If testing out menswear taught me one thing, it’s that low-rise pants aren’t as bad as everyone thinks.

Everyone has black leather loafers—try something different with this lighter suede pair instead.

I’ve spotted this Banana Republic flight jacket on at least a dozen fashion industry guys, from stylist Justin Boone to publicist Lindsey Solomon, but rarely any women, so I wanted to test it out myself. I paired the ultra-cozy, shearling coat with a pair of ACNE Studios trousers that I bought off my boyfriend (he’d had them tailored too small so they actually fit me pretty well). The two-tone heels perfectly pulled the look together.

Wearing: Banana Republic Heritage Shearling Flight Jacket ($1300); Acne Studios pants; Wandler shoes.

I’ve been seeing this flight jacket in various forms all over Instagram and TikTok lately. 

If you’re not in the mood to scour through racks of men’s khakis at your neighborhood thrift shop, this pair from J.Crew will absolutely do the trick.

These heels are the perfect add-on to elevate this look.

Similar to the aforementioned ACNE Studios khakis, I first got the idea to buy vintage men’s army pants after I stole a pair from my boyfriend and wore them to New York Fashion Week in September. I loved them so much that I began researching secondhand styles and sizes, eventually settling on this super baggy pair. Once it’s warm out, I plan to solely wear them with bra and bikini tops, but for now, I’m loving them with this cropped Ganni bomber and my go-to Adidas Sambas (also from the men’s section). 

Wearing: Ganni Recycled Nylon Jacket ($295); Adidas Samba Classic Indoor Soccer Shoe ($85)

Because of how slim this bomber is, it’ll pair perfectly with baggy pants.

While there is an endless array of vintage army pants available on sites like eBay and Etsy, these Madewell utility pants are a great alternative.

I wear these at least twice a week.

This look is giving off The Frankie Shop vibes like crazy.

All the style of a men’s three-piece suit with a perfectly tailored fit.

I love “dad” jeans.

This baseball cap is so simple yet so cool.

That slouchy fit, though.

I think about these Saint Laurent loafers a lot.

This color is top notch.

The perfect layering piece.

I want to wear this rugby-style sweater on a daily basis.

Let’s play a game of is this menswear or is it womenswear, shall we?

When your PJs double as ready-to-wear.

They’re called “dad sneakers” for a reason.

The fashion version of your brother’s old sweatpants.

One day very soon, I’m going to buy this leather bomber.

It’s the asymmetric detailing for me.

Next, This Is How Fashion Girls Will Be Wearing Denim in 2023, Period

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