The popularity of the tomboy look on the streets has never been more prevalent than now. While feminine silhouettes will never go out of style, there is an inherent coolness to all of the slouchy sweaters, fancy suits, boyfriend jeans, and combat boots that we’ve been spotting as of late. Not only is this look extremely comfortable, but it also embraces a functional and versatile aesthetic that is instantly appealing. In the gallery below, you’ll find 25 tomboy street-style looks, plus tips on how to make them your own.
Elevate tomboy skater style and its baggy proportions with an iconic trench for a look that’s as comfortable as it is cool.
Brand-wise, Céline is a bastion of tomboy styles, and this maroon-clad model is clearly a Célinephile.
This adorable street-style model plucks a look directly from the greaser category, straight down to her pompadour and combat boots.
Lily Donaldson dishes a big dose of tomboy style in an on-trend combination of crop top, tiny backpack, and Gucci loafers.
Sporty Spice, the iconic tomboy of the 90s, is channelled into this look with a cropped tank, track pants, and, of course, plenty of attitude.
Tomboy style can still be très chic – simply add a duster and skinny scarf to the mix.
Tomboy style doesn’t have to be quiet; in fact, you can be as bold as you want to be. Bright orange hues and brilliant patterns make this masculine look one worthy of fashion week.
Layer up the masculine way by choosing oversized pieces and off-kilter proportions, like this street-style star.
A monochrome, minimalist approach to tomboy style straddles the worlds of masculinity and chicness.
Re-appropriate joggers from your gym bag and snag a cool bomber for an effortless tomboy look.
Once you’ve got the outfit down, your next task is to perfect the slouch-against-the-wall pose that influencers love to post on Instagram.
This look is less “boy” than “man”. A grown up, polished look like this is achieved by impeccable tailoring and smart layered menswear.
Tomboy style can also be cute; fun accessories are an easy outfit enhancement that you can utilize to make the look your own.
Varsity jackets are no longer symbols of love from high-school sweethearts but serious style staples of the tomboy wardrobe.
Flip the script by taking feminine colors like pink and purple and wearing them in slouchy, loose-fitting silhouettes.
Tomboy attitude comes through loud and clear in a sporty, all-black ensemble finished with tough hiking boots and “leave-me-alone” headphones.
Pull off a polished version of the tomboy look in more fitted shapes and masculine footwear.
Schoolgirl style and tomboy style have a lot in common – just switch out the skirt for trousers and you’re good-to-go.
Yes, you can absolutely take a more feminine piece – like a frilly blouse – and tomboy it up with basics like denim and loafers.
There are so many different ways to rock the tomboy look, and one that never gets old is the “Teddy Boy” style born on Savile Row. This leather jacket and high-necked blouse really nail a modern version of the look.
Plenty of classic wardrobe pieces originated in the realm of menswear, so don’t be shy about mixing and matching them, like this cool trench-and-denim combination.
A checkered suit is completely of-the-moment for 2020, but those feminine accessories put a new spin on the style.
Make current trends – like the mini bag – work within a larger framework of tomboy style when you pair them with smart foundational pieces, like leather trousers.
You can say yes to a dress and still retain your tomboy identity. The trick? Adding massively intimidating combat boots to your look.