How To Pull Off Tomboy Style Without Looking Like A Dude

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.

White Button-Down Shirt + Leather Shorts + Combat Boots = Model Off-Duty Cool


Vanessa Jackman

Blazer + Slouchy T-Shirt + Simple Pumps = Tomboy-Inspired Outfit For Work


Style du Monde

Sweatshirt + Sneaker + Cross-Body Bag = Perfect Outfit For Running Errands


Vanessa Jackman
Chambray Button-Down Shirt + Undone Overalls + Sleek Ponytail = Tomboy, The Cute Way


Style du Monde
Button-Down Shirt + Rolled Skinny Jeans + Buckled Loafers = Tomboy Minimalism


Style du Monde
Layered Tops + Denim Cut-Offs + Shiny Loafers = What We Want To Wear Every Weekend


Style du Monde
Hoodie + Slouchy Pants + Luxe Satchel = Comfortable, Yet Chic


Style du Monde

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.

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.


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.

3.1 Phillip Lim Draped Pocket Trousers ($375) in White

The perfect slouchy summer pants, for work and beyond.

J.Crew Collection Leather Motorcycle Jacket ($1,200) in Navy

Yes, you read correctly: a NAVY moto jacket. It does exist.

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.

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.

Vince Manny Boyfriend Shorts ($175) in Summer Vintage

This summer staple offers a flattering slim fit and modest hemline for the win!

Larsson & Jennings Lader Watch ($334) in Black

We’re obsessed with this watch, for good reason: dainty menswear at its best. 

McQ Alexander McQueen Grace Leather Point-Toe Flats ($345)

The simplicity and pointed toe of these flats equals tomboy chic done right. 

Zara Denim Waistcoat ($60) in Light Blue

This vest will give any outfit (even a girly dress) a touch of tomboy.

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!

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