A Street Style Guide to Tomboy-Inspired Fashion

Kristen Bousquet
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STYLECASTER | Street Style Guide to Tomboy Fashion
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Photo: STYLECASTER/Getty Images

Gender-neutral is a buzzy term these days, and we don’t see why that trend shouldn’t extend to fashion. Tomboyish style may not be a groundbreaking sartorial concept, but it feels particularly on point in 2018, when traditional gender roles and markers are less relevant than ever. Rather than considering menswear-inspired looks to be “borrowed from the boys,” we see hoodies, jogger pants and sneakers as chic elements of any woman’s wardrobe.

MORE: 20 Perfect Fashion Combos That Will Never Go Out of Style

And, though any person with any body type and gender preference (or lack thereof) certainly has the ability to rock any look, pattern, silhouette, or color scheme—whether it’s graphic tees and boyfriend jeans or florals and lace—there’s no denying there’s something so sexy about a woman who’s comfortable enough with herself to wear something that’s less traditionally feminine (or traditional, period).

Ahead, check out dozens of ideas for how to pull off the perfect tomboyish look—styling and shopping included.

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STYLECASTER | Tomboy Outfits | Street style star wearing oversized teddy jacket
Photo: Getty
STYLECASTER | Tomboy Outfits | Street style star wearing hoodie and leather leggings
Photo: Getty
STYLECASTER | Tomboy Outfits | Z Supply The Camo Overalls

Z Supply The Camo Overalls, $79 at Z Supply

STYLECASTER | Tomboy Outfits | Street style star wearing leather pants and sneakers
Photo: Getty
STYLECASTER | Tomboy Outfits | Street style star wearing hoodie and boyfriend jeans
STYLECASTER | Tomboy Outfits | J.O.A. wide leg jumpsuit with sleeve ties

J.O.A. wide leg jumpsuit with sleeve ties, $95 at J.O.A.

STYLECASTER | Tomboy Outfits | Street style star wearing jeans and button down shirt
Photo: Getty
STYLECASTER | Tomboy Outfits | Street style star wearing sweatshirt and leather jacket
Photo: Getty
STYLECASTER | Tomboy Outfits | DL1961 Bella high rise vintage slim

DL1961 Bella high rise vintage slim, $250 at DL1961

STYLECASTER | Tomboy Outfits | Street style star wearing army green pants and cropped top
Photo: Getty
STYLECASTER | Tomboy Outfits | Street style star wearing baggy pants and hoodie
Photo: Getty
STYLECASTER | Tomboy Outfits | Genuine People high waisted tulip pants

Genuine People high waisted tulip pants, $185 at Genuine People

STYLECASTER | Tomboy Outfits | Street style star wearing ripped jeans
Photo: Getty
STYLECASTER | Tomboy Outfits | Street style star wearing oversized sweatshirt
STYLECASTER | Tomboy Outfits | Joah Brown cocoon hoodie

Joah Brown cocoon hoodie, $68 at LIT Boutique

STYLECASTER | Tomboy Outfits | Street style star wearing sweater and boyfriend jeans
Photo: Getty
STYLECASTER | Tomboy Outfits | Street style star wearing silver boors and oversized hoodie
Photo: Getty
STYLECASTER | Tomboy Outfits | Z Supply The Lush Modal jogger pants

Z Supply The Lush Modal jogger pants, $65 at Z Supply

STYLECASTER | Tomboy Outfits | Street style star wearing floral skirt and bold sweater
Photo: Getty
STYLECASTER | Tomboy Outfits | Street style star wearing oversized sweatshirt
Photo: Getty
STYLECASTER | Tomboy Outfits | First Love black and red velvet joggers

First Love black and red velvet joggers, $78 at TOBI

STYLECASTER | Tomboy Outfits | Street style star wearing graphic tee and boyfriend jeans
STYLECASTER | Tomboy Outfits | Griffith Park medium wash distressed boyfriend jeans

Griffith Park medium wash distressed boyfriend jeans, $49 at Lulus

STYLECASTER | Tomboy Outfits | Street style star wearing flannel around the waist
Photo: Getty
STYLECASTER | Tomboy Outfits | TOBI Casey white low top sneakers

TOBI Casey white low top sneakers, $48 at TOBI

STYLECASTER | Tomboy Outfits | Street style star wearing blue hoodie
Photo: Getty
STYLECASTER | Tomboy Outfits | Others Follow Hudson washed purple hoodie

Others Follow Hudson washed purple hoodie, $62 at Lulus

STYLECASTER | Tomboy Outfits | Street style star wearing denim overalls
STYLECASTER | Tomboy Outfits | Modcloth Same Shirt Over There graphic t-shirt

Modcloth Same Shirt Over There graphic t-shirt, $29 at Modcloth

STYLECASTER | Tomboy Outfits | Street style star wearing baggy pants and hoodie
Photo: Getty
STYLECASTER | Tomboy Outfits | Nasty Gal Makin' a Camo Appearance hoodie

Nasty Gal Makin' a Camo Appearance hoodie, $30 at Nasty Gal

STYLECASTER | Tomboy Outfits | Street style star wearing jeans and oversized hoodie
Photo: Getty
STYLECASTER | Tomboy Outfits | Entourage Denver top in blue

Entourage Denver top in blue, $26 at Entourage

STYLECASTER | Tomboy Outfits | Street style star wearing graphic tee
Photo: Getty
STYLECASTER | Tomboy Outfits | Dolce Vita Pixyl flats

Dolce Vita Pixyl flats, $120 at Dolce Vita

STYLECASTER | Tomboy Outfits | Street style star wearing military jacket and leather pants
STYLECASTER | Tomboy Outfits | Nasty Gal Wednesday sweater

Nasty Gal Wednesday sweater, $38 at Nasty Gal

STYLECASTER | Tomboy Outfits | Street style star wearing camo pants
Photo: Getty
STYLECASTER | Tomboy Outfits | Street style star wearing leather pants and boots
Photo: Getty

Next slideshow starts in 10s

Stunning Hair and Makeup Looks at the 2018 SAG Awards

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  • STYLECASTER | Tomboy Outfits | Street style star wearing oversized teddy jacket
  • STYLECASTER | Tomboy Outfits | Street style star wearing hoodie and leather leggings
  • STYLECASTER | Tomboy Outfits | Z Supply The Camo Overalls
  • STYLECASTER | Tomboy Outfits | Street style star wearing leather pants and sneakers
  • STYLECASTER | Tomboy Outfits | Street style star wearing hoodie and boyfriend jeans
  • STYLECASTER | Tomboy Outfits | J.O.A. wide leg jumpsuit with sleeve ties
  • STYLECASTER | Tomboy Outfits | Street style star wearing jeans and button down shirt
  • STYLECASTER | Tomboy Outfits | Street style star wearing sweatshirt and leather jacket
  • STYLECASTER | Tomboy Outfits | DL1961 Bella high rise vintage slim
  • STYLECASTER | Tomboy Outfits | Street style star wearing army green pants and cropped top
  • STYLECASTER | Tomboy Outfits | Street style star wearing baggy pants and hoodie
  • STYLECASTER | Tomboy Outfits | Genuine People high waisted tulip pants
  • STYLECASTER | Tomboy Outfits | Street style star wearing ripped jeans
  • STYLECASTER | Tomboy Outfits | Street style star wearing oversized sweatshirt
  • STYLECASTER | Tomboy Outfits | Joah Brown cocoon hoodie
  • STYLECASTER | Tomboy Outfits | Street style star wearing sweater and boyfriend jeans
  • STYLECASTER | Tomboy Outfits | Street style star wearing silver boors and oversized hoodie
  • STYLECASTER | Tomboy Outfits | Z Supply The Lush Modal jogger pants
  • STYLECASTER | Tomboy Outfits | Street style star wearing floral skirt and bold sweater
  • STYLECASTER | Tomboy Outfits | Street style star wearing oversized sweatshirt
  • STYLECASTER | Tomboy Outfits | First Love black and red velvet joggers
  • STYLECASTER | Tomboy Outfits | Street style star wearing graphic tee and boyfriend jeans
  • STYLECASTER | Tomboy Outfits | Griffith Park medium wash distressed boyfriend jeans
  • STYLECASTER | Tomboy Outfits | Street style star wearing flannel around the waist
  • STYLECASTER | Tomboy Outfits | TOBI Casey white low top sneakers
  • STYLECASTER | Tomboy Outfits | Street style star wearing blue hoodie
  • STYLECASTER | Tomboy Outfits | Others Follow Hudson washed purple hoodie
  • STYLECASTER | Tomboy Outfits | Street style star wearing denim overalls
  • STYLECASTER | Tomboy Outfits | Modcloth Same Shirt Over There graphic t-shirt
  • STYLECASTER | Tomboy Outfits | Street style star wearing baggy pants and hoodie
  • STYLECASTER | Tomboy Outfits | Nasty Gal Makin' a Camo Appearance hoodie
  • STYLECASTER | Tomboy Outfits | Street style star wearing jeans and oversized hoodie
  • STYLECASTER | Tomboy Outfits | Entourage Denver top in blue
  • STYLECASTER | Tomboy Outfits | Street style star wearing graphic tee
  • STYLECASTER | Tomboy Outfits | Dolce Vita Pixyl flats
  • STYLECASTER | Tomboy Outfits | Street style star wearing military jacket and leather pants
  • STYLECASTER | Tomboy Outfits | Nasty Gal Wednesday sweater
  • STYLECASTER | Tomboy Outfits | Street style star wearing camo pants
  • STYLECASTER | Tomboy Outfits | Street style star wearing leather pants and boots

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