How to Dress Like a Tomboy – 3 Outfits of Cool Masculine Charm

Weekly Newsletter

Keep up with the latest in fashion, beauty and style!

The Tomboy style is a way of dressing popularized by music icons Patti Smith and Joan Jett in the 70s and 80s and comprised of men’s denim jeans, oversized T-shirts, jackets, and athletic wear as an alternative to traditional feminine fashion.

Patti Smith and Joan Jett's Tomboy Style
Patti Smith and Joan Jett’s Tomboy Style

With an unpretentious and straightforward look, the Tomboy style depicts women of high resilience, straightforwardness, active lifestyle, and confidence to challenge traditional gender norms.

Tomboy fashion style outfits

In this article, I’ll introduce you to 3 Tomboy outfits, ideal for showcasing confidence, resilience, and an active lifestyle.

1. Rocker Tomboy

Rocker Tomboy

Apperloth A Zip Up PU Leather Moto Jacket
 Women's Hooded Sweatshirt With Exposed Seams And Drawstrings Ripped Mom Fit Jeans
Unisex Punk Style Double Layer Metal Decor Chain Pants Chain Vans Cruze leather trainers in white

Start the Rocker Tomboy look with a classic bike leather jacket, a key garment to any rocker-inspired wardrobe, ideally from Schott NYC, renowned for iconic pieces associated with rock culture.

Lara Bingle and Kristen Stewart in leather biker jackets

Pair with black ripped and distressed skinny jeans from Rag & Bone, capturing the rocker aesthetic, and a standout silver chain from A.P.C. for a touch of boyish chic.

Kendall Jenner and Zendaya in ripped boyfriend jeans

Complete the look with high-top Italian sneakers from Common Projects, a sleek and minimalist alternative to the classic Converse.

2. Skater Tomboy

Skater Tomboy fashion style outfit

Women's Compton Embroidery Baseball Cap Tie Dye Knit Loose Fit Women's T-Shirt High Waist Mom Fit Jeans
Vans SK8-Hi trainers in white How to Dress Like a Tomboy - 3 Outfits of Cool Masculine Charm

Start the Skater Tomboy look with a black and white Baker oversized T-shirt from Baker Skateboards, a label that captures the essence of skater culture.

Vanessa Hudgens and Zendaya in oversized t-shirts

Complement the tee with a pair of Levi’s 501 Skateboarding Jeans designed to hold up against the wear and tear of skateboarding, and top off the look with a black Stussy strapback cap, a brand deeply rooted in skate and streetwear culture.

Cindy Crawford and Courtney Cox in Levi's jeans

Accessorize with a Seiko sports watch and white Old Skool Vans sneakers, another icon of the skateboarding world, to capture the essence of the skater tomboy style with a balance of iconic branding.

3. Alt Tomboy

Alt Tomboy fashion style

Grunge Punk Slogan Graphic Drop Shoulder Tee Camo Print Flap Pocket Side Drawstring Waist Cargo Pants
Lace-up Front Combat Boots
Black TPU Strap Sporty Square Dial Digital Watch, For Daily Life Letter Patch Knit Hat

The Alt Tomboy look is a fashion statement that draws from alternative subcultures.

Start with an authentic Black Sabbath classic tee from a vintage store, camo cargo pants from Rothco for an edgy military vibe, and black army boots from Magnum.

Billie Eilish's Tomboy Style
Billie Eilish’s Tomboy Style

Accessorize with a black Tommy Hilfiger beanie for a branded touch that adds an element of mainstream streetwear and a Casio’s G-Shock watch in a nod to retro ’90s fashion.

Styling Tips

  • The Tomboy style confers traditionally masculine garments with a feminine twist.
  • Tomboy style has a rebellious and unconventional streak associated with a youthful, spirited attitude.
  • Compared to the tailored look of androgynous fashion and the Boyish style, Tomboys wear a more casual and sporty streetwear feel, comprised of oversized tees, jeans, and athletic apparel with a focus on comfort and functionality.
A Casual, Street-style Tomboy Outfit
A Casual, Street-style Tomboy Outfit

Similar Styles to Tomboy

Androgynous | Boyish | Skater | Mod | Teddy Girl | Indie

Weekly Newsletter

Keep up with the latest in fashion, beauty and style!

Style Like a Pro!

Are you looking to improve your fashion style and unsure where to start?

Contact The VOU’s style experts to receive your free and personalized styling advice based on your current way of dressing, preferred outfits, colors, aesthetics, age, gender, body shape, location, and event you seek to attend.

A passionate advocate for inclusivity and diversity, Aidan is the driving force behind The VOU magazine as its Editorial Manager. With a unique blend of editorial acumen and project management prowess, Aidan's insightful articles have graced the pages of The Verge, WWD, Forbes, and WTVOX, reflecting his deep interest in the dynamic intersection of media and technology.

Similar Articles


Please enter your comment!
Please enter your name here

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.