What To Borrow From The Boys

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Blurred gender lines have received a lot of attention as of late, but it has been de rigueur in the fashion world since Coco Chanel started wearing pants. In honor of the timeless trend, we’ve outlined the simple rules of menswear-inspired dressing. Time to suit up!

Schoolboy Stripes

Taking its inspiration from traditional boys' school uniforms, a bold vertical-stripe shirtdress looks sharp enough for roll call.

All Photos: Adam Katz Sinding

Stripe Twill Collar Dress

$500

Anna K

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Boiler Suit

The rough-and-tumble staple (originally reserved for mechanics) gets a fashion-forward spin via mules and a silk neck scarf.

Denim Boilersuit

$125

Topshop

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Sailor Watch

Instead of a delicate bracelet style or oversize menswear band, the nautical-strap of this watch feels unexpected and fresh.

Women’s Multi-Function Watch

$150

Vince Camuto

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Lightweight Suit

A cropped seersucker or linen suit looks particularly dapper when paired with brogues and a floppy hat. For the less tomboy inclined, try a knit tank and sandals.

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Striped Suit Trousers

$60

Mango

Striped Suit Jacket

$100

Mango

Sensible Footwear

We love a flat shoe, and most menswear ensembles look better with them as a finishing touch. Complete your outfit with a minimal, white sneaker.

Bart Leather Sneaker

$480

Isabel Marant

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Tailored Trouser

Everyone needs a tailored trouser—the perfect midpoint between a stovepipe skinny and relaxed wide leg—to pair with everything from moto jackets and heels to boots and a vintage T-shirt.

Navy Tailored Pants

$467

Jill Sander

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Sharp Shirt

Instead of a classic striped shirt, try a plaid or retro print for an unexpected take on menswear.

Cicala Plaid Slim Fit Shirt

$20

Stella Jean

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