How To Pull Off Tomboy Style Without Looking Like A Dude

How To Pull Off Tomboy Style Without Looking Like A Dude
Stockholm Street Style

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.

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

    PHOTO: Vanessa Jackman
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    Blazer + Slouchy T-Shirt + Simple Pumps = Tomboy-Inspired Outfit For Work

    PHOTO: Style du Monde
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    Sweatshirt + Sneaker + Cross-Body Bag = Perfect Outfit For Running Errands

    PHOTO: Vanessa Jackman
  • 4 of 24

    Plaid Blazer + All-White Staples + Monk-Strap Flats = Cool-Girl Summer Outfit

    PHOTO: Stockholm Street Style
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    Bomber Jacket + Cross-Body Bag + Black Skinny Jeans = Feminine Accessories For The Win

    PHOTO: Stockholm Street Style
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    Chambray Button-Down Shirt + Undone Overalls + Sleek Ponytail = Tomboy, The Cute Way

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

    PHOTO: Style du Monde
  • 8 of 24

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

    PHOTO: Style du Monde
  • 9 of 24

    Black and White Essentials + Metallic Sliders + Backpack = Chic Accessories Are Everything

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    Hoodie + Slouchy Pants + Luxe Satchel = Comfortable, Yet Chic

    PHOTO: Style du Monde
  • 11 of 24

    Statement Jacket + Overalls + Combat Boots = The ‘90s Redux Version Of Tomboy

    PHOTO: Gastro Chic
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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.

  • 18 of 24

    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.

  • 20 of 24

    Vince Manny Boyfriend Shorts ($175) in Summer Vintage

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

  • 21 of 24

    Larsson & Jennings Lader Watch ($334) in Black

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

  • 22 of 24

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

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

  • 23 of 24

    Zara Denim Waistcoat ($60) in Light Blue

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

  • 24 of 24

    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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