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Apr 26, 2016 @ 5:00 pm

I’ve always half-seriously joked that I can remember each of my significant romantic relationships by the menswear pieces I stealthily commandeered during them. Maybe it’s my poor circulation and comparatively warm heart, but I always seem to end romantic interludes with more hoodies than regrets.

My penchant for wearing significant others’ clothing reached an all time high when I was dating my ex, John (names have notably not been changed to protect the innocent). I posit that this was influenced by the fact that he was my first love interest that was not only stylish, but was also almost my height. Regardless, I amassed so much of his clothing during our relationship, that when we broke up my roommate suggested I give his clothes away to strangers in the street and create a cathartic breakup Tumblr (though I was tempted — the break-up was not good — I did *not* act on her idea).

After my relationship with John ended, I truly realized how much I missed having menswear as a regular sartorial option, and thus began a quest to purposely include it in my wardrobe. Below, based on my extensive research, in my humble opinion, are the five types of clothing that are just better in menswear. 

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I vividly remember visiting John’s family over the 4th of July and realizing, quickly, that it was far colder in Buffalo than I realized, even in the height of summer. After freezing for a whole day in my shorts, John offered to let me borrow his jeans for the evening to stay warm. Let me just tell you guys, men’s jeans are awesome. 


I love the baggy, almost-falling-off-look, and as a bonus you can buy men’s jeans in sizes that specify both the length of the inseam *and* the waist size, so that you aren’t stuck dealing the BS of figuring out what actual size you are in whatever brand of women’s clothing you’re buying. The key, in my opinion, to wearing men’s jeans (or even the disappointingly-heteronormatively-named “boyfriend” jeans) is to pair them with a tailored top. Though, I must admit, I often enjoy wearing my favorite ripped men’s jeans with a baggy, comfy, guy’s sweatshirt.

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You can argue that men’s hoodies are pretty much the same as women’s hoodies — but I think what makes men’s hoodies and pullover sweatshirts better is the “comfiness factor” (this is a technical term, of course). 

Kourt x Khlo = Everything

A photo posted by Khloé (@khloekardashian) on

There’s nothing more relaxing than throwing on an oversized men’s sweatshirt and leggings to run to the gym, run errands, or rock the athletic-chic Khloe Kardashian look.

My Favorites:


Topman LTD Black Textured Sweatshirt $65 & Play the Bones Unisex Sweatshirt $151


Similarly to sweatshirts, they do make women’s flannels, but in my experience they are sized down, tailored at the waist and chest, and come in more traditional “feminine” gender-normative colors. That is just not my jam. I love real, straight-cut, huge men’s flannels that can swallow you right up (and not gape open at your chest, because why do women's button downs always do that??). They’re awesome to wear with shorts at the beach, or with skinny women’s jeans and combat boots in the winter.

My Favorite:


Uniqlo Men’s Flannel Long Sleeve Shirt $5.90

Boots and Shoes

Speaking of boots; this may be slightly unique to my situation, but I love buying men’s shoes. I have pretty big feet (women’s size 10.5 what’s gooodddd), and I find that most women’s versions of iconic shoe styles — think combat boots, hiking boots, high top sneakers, etc. — look strangely cartoonish when sized up to 10.5. 


Additionally, I don’t have particularly narrow feet (read: they are wide af), so the width of a men’s 8.5 sized Timbaland boot is much more comfortable than the comparatively sized women’s version.

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Pictured: Alpha Industries MA-1 Slim Fit Flight Jacket $140

Lastly, one of my most important menswear addictions is my love for men’s jackets and coats. I love the broad shouldered, slightly oversized look of a men’s bomber jacket, peacoat, or leather jacket, and they are also great for layering with tons of sweaters and scarves in the winter.

Bonus: Accessories

I used to have a disconcerting and embarrassing habit of flirting with men by trying on their watches (what can I say, I was 23 and going out in Meatpacking, my taste was already questionable).

After I once almost wandered off with a conquest’s exorbitantly overpriced watch (my apologies, 35-year-old Swedish lawyer), I decided that a better tactic would be to buy my own men's watch to wear. I like the larger watch faces and the wider bands of men's watches, and I always prefer accessories in silver and black as opposed to white and gold.

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Though my collection isn't yet as extensive as I'd like, I often find I prefer my menswear options to my women's clothing — even without a boyfriend to steal from. What menswear looks do you love to wear (or steal from friends, relatives, or lovers)?