You don’t have to actually be a tomboy to dress like one. The key to making this look work is to throw in just a touch of femininity, whether it’s via a slightly pointed shoe, a few undone buttons on your shirt, or some golden hardware on your satchel. Scroll down to take a cue from these on-point street style examples, and see some of the best items to take you to tomboy territory.
How To Pull Off Tomboy Style Without Looking Like A Dude
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White Button-Down Shirt + Leather Shorts + Combat Boots = Model Off-Duty Cool
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Blazer + Slouchy T-Shirt + Simple Pumps = Tomboy-Inspired Outfit For Work
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Sweatshirt + Sneaker + Cross-Body Bag = Perfect Outfit For Running Errands
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Plaid Blazer + All-White Staples + Monk-Strap Flats = Cool-Girl Summer Outfit
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Bomber Jacket + Cross-Body Bag + Black Skinny Jeans = Feminine Accessories For The Win
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Chambray Button-Down Shirt + Undone Overalls + Sleek Ponytail = Tomboy, The Cute Way
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Button-Down Shirt + Rolled Skinny Jeans + Buckled Loafers = Tomboy Minimalism
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Layered Tops + Denim Cut-Offs + Shiny Loafers = What We Want To Wear Every Weekend
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Black and White Essentials + Metallic Sliders + Backpack = Chic Accessories Are Everything
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Hoodie + Slouchy Pants + Luxe Satchel = Comfortable, Yet Chic
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Statement Jacket + Overalls + Combat Boots = The ‘90s Redux Version Of Tomboy
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Slouchy Shirt + Skinny Boyfriend Jeans + Hair Tucked Up = Tomboy, The Sexy Way
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AG Adriano Goldschmied The Nikki Crop Jeans ($198) in 17 Years Lifted
These slightly skinny cropped jeans with perfectly placed rips are one of the most flattering pairs of boyfriend jeans we’ve seen.
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Madewell Oversized Button-Down Shirt ($75) in Optic White
We’re constantly on the hunt for a borrowed-from-the-boys shirt that doesn’t look ridiculous. Thank you, Madewell.
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Sophie Hulme Soft Flap Bag ($780) in Black
Tomboys still have to carry stuff. This satchel is akin to a jazzed-up briefcase but with sleek touches of gold hardware.
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3.1 Phillip Lim Draped Pocket Trousers ($375) in White
The perfect slouchy summer pants, for work and beyond.
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J.Crew Collection Leather Motorcycle Jacket ($1,200) in Navy
Yes, you read correctly: a NAVY moto jacket. It does exist.
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Saint Laurent Flat Top Aviator Sunglasses ($395) in Rose Gold/Grey
Thanks to the rose gold and unique shape, these aviators just leapt to the top of our wish list.
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Equipment Brett Shirt With Contrast ($268) in Klein Blue/Black Military Stripe
It’s like your boyfriend’s shirt, but cooler, thanks to contrasting stripes and a fitted style.
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Vince Manny Boyfriend Shorts ($175) in Summer Vintage
This summer staple offers a flattering slim fit and modest hemline for the win!
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Larsson & Jennings Lader Watch ($334) in Black
We’re obsessed with this watch, for good reason: dainty menswear at its best.
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McQ Alexander McQueen Grace Leather Point-Toe Flats ($345)
The simplicity and pointed toe of these flats equals tomboy chic done right.
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Zara Denim Waistcoat ($60) in Light Blue
This vest will give any outfit (even a girly dress) a touch of tomboy.
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Stuart Weitzman Zipit High Top Sneakers ($435) in Black
A sneaker-combat hybrid with edgy details will add tomboy coolness to almost any outfit.
Tell us how you feel about tomboy style in the comments below!