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How to Wear It: Menswear for Women

@sarah_jade_huntsville in her Classic Iconic Racer Jacket in Light Pink

There’s just something about menswear for women. Whether it’s your significant others or something you picked up at the thrift store, menswear for women will forever be in style. If you’ve amassed more than just an oversized sweatshirt and are ready to take menswear to the streets, we’ve got your guide.

Pair a Button-Down Shirt with Flares

Before you let your significant other toss their favorite button down, steal it to wear for yourself. If it’s a solid color, pair with a striped tee and dark blue fares with hoop earrings. If it’s patterned, try pairing with a print or graphic tee and light or dark blue flares.

The Weekend Edition: Joggers

Pair your favorite oversized tee with a pair of joggers, leather (or faux leather) biker jacket and fashion sneakers for a relaxed weekend look. Bonus points if the tee is a vintage 80’s rock band tee. We’re pretty sure you’ll win best dressed at brunch…

An Oversized Sweatshirt

For the perfect anytime outfit, pair your favorite oversized sweater with a pair of mom jeans, Keds, and a long trench coat. The perfect sweatshirt for this look? A vintage Champions sweatshirt. If you’re feeling like dressing it up a bit, try pairing a witty oversized sweatshirt, distressed denim, a military-inspired coat, and a pair of heeled sandals.

Return of the Plaid

 Because there is no shortage of oversized plaid shirts at a thrift store, why not make an outfit out of it by pairing it with a pair of white jeans, a patch-heavy denim jacket, and some sleek black mules. If you aren’t feeling the white jeans, a pair of black jeans will look just as awesome.

The Canadian Tuxedo

Who doesn’t love denim on denim? Borrow (or steal, no judgements here) that oversized denim jacket and pair with a long-sleeve sweater, cut-off shorts in the same color family as the denim jacket, and a pair of fun, bright sandals.

Going Up, Going Out

If you’ve got an oversized shirt that you’re looking to wear on a night out rather than for weekend brunch, try pairing it with sleek faux leather pants and a faux suede moto jacket. For accessories, try a couple 90s inspired chokers.

Everyone’s Favorite Bomber Jacket

We can’t mention menswear for women without the classic bomber jacket. Try pairing your favorite Classic Iconic Racer jacket with a floral romper, large round sunglasses, and some fashion sneakers for an on-point spring outfit.  

@thejessicaexperience in the Classic Iconic Racer Jacket in Wheat 

If you’re a fan of anything and everything oversized, the menswear for women trend is perfect for you. If you’re more of the “I only like my jackets oversized” type, make sure to check out the Members Only men’s apparel for women collection here. We have everything from denim jackets to sweaters to the Classic Iconic Racer jacket.


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