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.
Swap your ballet flats for printed slip-ons.
Steal your boyfriend’s graphic t-shirt and pair it with high-top sneakers.
Pair an oversized graphic tee with a backwards flat-brim cap.
Team a schoolboy cardigan with a pair of low-slung jeans.
Evoke a ‘90s hip-hop vibe with baggy trousers and a pair of basketball sneakers.
Show your team spirit with a baseball hat.
Go casual with a pair of slouchy distressed shorts and lace-ups.
Channel a ‘50s greaser with a leather jacket, cuffed skinny jeans, and a pompadour hairstyle.
Layer a biker jacket over an unbuttoned flannel shirt.
Add an extra dose of nonchalance to a worn-in tee by knotting a sweatshirt around your waist.
Red Glazed Leather High-Top Sneakers ($250)
Lyon Asai Pant ($245)
The LA Denim Cap ($38)
Boyfriend Roll-Up Shorts ($40)
Baseball Tee ($125)
Mill Leather Davis Brief ($425) in Chocolate
Neck-Tie Charmeuse Blouse ($595)
Double Sleeve Shirt ($238)
M Jersey Varsity Bomber Jacket ($70)
Babe Brogue Oxfords ($49)
Light V Neck Cardigan ($30) in Green
Boyfriend Jeans ($60)

Jessica Baker has 16 years of experience in the digital editorial fashion and entertainment space. She is currently the Executive Director, Entertainment at Who What Wear where she ideates, books, writes, and edits celebrity and entertainment features.