The Essentials For Dressing Like A Tomboy

Girls like Kristen Stewart, Cara Delevingne, and Agyness Deyn have tomboy dressing down to a science. The formula is simple: combine equal parts cool girl attitude and the right borrowed-from-the-boys fashion for enviably nonchalant off-duty outfits. We could all learn a thing or two from these style-minded influencers, which is why we’re spotlighting some of our favorite must-try tomboy looks followed by a roundup of menswear-inspired essentials you can shop now. Keep reading for key styling tips and more.

Diane Kruger

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Pacific Coast News

Swap your ballet flats for printed slip-ons. 

Analeigh Tipton

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Fame Flynet

Steal your boyfriend’s graphic t-shirt and pair it with high-top sneakers. 

Miley Cyrus

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Fame Flynet

Pair an oversized graphic tee with a backwards flat-brim cap. 

Gwyneth Paltrow

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INF

Team a schoolboy cardigan with a pair of low-slung jeans.

Cara Delevingne

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Splash News

Evoke a ‘90s hip-hop vibe with baggy trousers and a pair of basketball sneakers. 

Chloe Sevigny

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Fame Flynet

Show your team spirit with a baseball hat. 

Rihanna

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Splash News

Go casual with a pair of slouchy distressed shorts and lace-ups. 

Michelle Williams

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Startraks

Channel a ‘50s greaser with a leather jacket, cuffed skinny jeans, and a pompadour hairstyle.

Agyness Deyn

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Xposure

Layer a biker jacket over an unbuttoned flannel shirt. 

Kristen Stewart

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Xposure

Add an extra dose of nonchalance to a worn-in tee by knotting a sweatshirt around your waist. 

Denim Refinery

The LA Denim Cap ($38)

Jack Spade

Mill Leather Davis Brief ($425) in Chocolate

Peter Jensen

Double Sleeve Shirt ($238)