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.

main

Diane Kruger
(Image credit: Pacific Coast News)

Swap your ballet flats for printed slip-ons. 

main

Analeigh Tipton
(Image credit: Fame Flynet)

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

main

Miley Cyrus
(Image credit: Fame Flynet)

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

main

Gwyneth Paltrow
(Image credit: INF)

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

main

Cara Delevingne
(Image credit: Splash News)

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

main

Chloe Sevigny
(Image credit: Fame Flynet)

Show your team spirit with a baseball hat. 

main

Rihanna
(Image credit: Splash News)

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

main

Michelle Williams
(Image credit: Startraks)

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

main

Agyness Deyn
(Image credit: Xposure)

Layer a biker jacket over an unbuttoned flannel shirt. 

main

Kristen Stewart
(Image credit: Xposure)

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

main

main

Marc by Marc Jacobs

Red Glazed Leather High-Top Sneakers ($250)

main

AllSaints

Lyon Asai Pant ($245)

main

Denim Refinery

The LA Denim Cap ($38)

main

Gap

Boyfriend Roll-Up Shorts ($40)

main

Harvey

Baseball Tee ($125)

main

Jack Spade

Mill Leather Davis Brief ($425) in Chocolate

main

Michael Kors

Neck-Tie Charmeuse Blouse ($595)

main

Peter Jensen

Double Sleeve Shirt ($238)

main

Topshop

M Jersey Varsity Bomber Jacket ($70)

main

Wanted

Babe Brogue Oxfords ($49)

main

Uniqlo

Light V Neck Cardigan ($30) in Green

main

Zara

Boyfriend Jeans ($60)

Executive Director, Entertainment

Jessica Baker is Who What Wear’s Executive Director, Entertainment, where she ideates, books, writes, and edits celebrity and entertainment features.