Tomboy Tricks: 4 Guy Styles That Look Great On Women

Tomboy Tricks: 4 Guy Styles That Look Great On Women

Tomboys are amazing creatures. When they enter a room you immediately know that something unique has happened. Not really boys but not like other girls, they charm and provoke us with their gender-fluid sensibilities and daring style. However, pulling together an outfit that expresses her personality and looks flattering can be a challenge.

True tomboy fashion is more than just culling jeans and bowties from the menswear section. It’s rejecting traditional notions of what makes a girl pretty and turning the word handsome on its head. While there are as many tomboy styles as there are tomboys, there are four eternal Tomboy looks that everyone should try at least once in their life.


Think pant suits and red lipstick when you go classic. The 1930’s and 40’s were the best time to see examples of this. Dietrich and Hepburn spring to mind. Gwen Stefani is the most recent icon to fully embrace this look, with her distressed denim, boots, printed tees and signature red lipstick.

Half Hollywood glamour, half punk rock, classic tomboy style is fun and pretty. These tomboys trade nylons and pencil skirts for trousers and riding breeches. They wear three-piece suits and high-heels. They wear makeup and combat boots. They embrace the glamour of being a woman and the practicality of clothes made with comfort in mind. Pro Tip: Sometimes you can even wear a skirt.


Unisex is not just a Japanese subculture anymore. Gender-bending makeup and fashion are going mainstream, pairing unisex haircuts with gender-neutral clothes to create a silhouette that is neither feminine nor masculine. Boyfriend jeans, sneakers, button-down shirts and funky accessories pull this look together.

It’s important to remember that Tomboys aren’t trying to look like boys. They just aren’t “that” kind of girl. So when choosing clothes for these styles, avoid anything that creates or emphasizes bulges in the silhouette. This includes belt buckles unless the shirt is tucked in. Grip belts and ratchet belts are a good option for this kind of style.

Street Style

This style is most heavily influenced by hip-hop culture and skater style. The high point of this style was the 90s. Many of the female groups played with this look, most notably TLC and Salt-N-Peppa.

Fortunately, the look is coming back, with a new twist. It’s sleeker and more understated than it used to be, without losing its roots. The oversized denim has been replaced by boyfriend jeans, joggers, and drop crotch pants. This look incorporates a lot of sports paraphernalia, snapbacks, Nikes, and Vans.


While the classic tomboy look is heavy on glamour, the dark or goth Tomboy is just glam. It too takes its cues from the past, pulling influences from the 70s, 80s and early 90s punk rock and heavy metal scenes. This look is a little bit emo, and a little bit goth, relying heavily on accessories and layering to pull it off.

This style is heavy on the eyeshadow, lipstick, and hair gel for “effect” rather than beauty. The dark Tomboy look is also very unisex, with boys and girls wearing the same clothes and styles. This is a great look for the days when you are channeling your inner Joan Jett.

Tomboys are always forcing us to redefine what it means to “dress like a lady”. They are living proof that you don’t have to be “girly” to be beautiful. Tomboy style isn’t just for Tomboys and the four looks described aren’t carved in stone.

You can mix and match to suit your mood (and your budget). So the next time you open your closet and feel like you have nothing to wear, try raiding your brother’s closet.