25 Hot Women Who Dress Like Men

Dresses Like: A ventriloquist's dummy
Occupation: Singer

Janelle is like a throwback to retro-1930s style. The singer's look—well, uniform really—consists of tuxedo pants paired with white button-downs and a bow-tie. Occasionally, she'll throw on a top hat over her signature pompadour. Throughout the years, she's become known for her monochromatic menswear looks just as much as her music and dance moves.

Dresses Like: Your office crush
Occupation: Model

Celia is one of the GOATs. The model, most known for her appearance on America's Next Top Model, has been wearing suits for as long as we can remember. And she sports them as everyday outfits. To her, there is no such thing as off-duty.

Dresses Like: The sixth man
Occupation: Fashion News Editor, Glamour

The perfect way to describe Rajni's look is "boy meets girl." She often dresses like a guy, but accessorizes like a woman, which means her menswear looks are never too masculine. We named her one of the most stylish women in New York and we're just as comfortable naming her one of the hottest women, too.

Dresses Like: A swagged-out grandpa
Occupation: Fashion Director, Esquire Singapore

Street style photographers thirst for Janie's swaggy old-man steez. Chances are, she's popped up on your Tumblr, blogs, and RSS Feeds dozens of times, usually rocking printed, linen blazers and pants, bow-ties and ties, as well as floppy fedoras. If you haven't seen her, then you've been looking at all the wrong places.

Dresses Like: A seapunk Eazy-E
Occupation: DJ

To say Venus X has eclectic style would be an understatement. The New Yorker is a style chameleon who can pretty much wear anything, and does. Some days that means mini skirts, other days it's baggy jeans and a white tee with Timbs. Either way, her personal style, which she describes as goth and hood, has a certain edge and toughness to it.

Dresses Like: A #menswear blogger
Occupation: VP Of Men's Sportswear and Shoes, Bergdorf Goodman

Bow your heads, kids. Mimi Fukuyoshi is one of the most respected, well liked, and knowledgeable people in the industry. Her fashion resume runs deep, having worked at Gilt Man, Bloomingdale's, and currently, as the Vice President of Men's Sportswear and Shoes at Bergdorf Goodman. She says she's not a tomboy—some days she wears heels and dresses—but you'd never know by the way she pulls off menswear looks.

Dresses Like: The cool chick that hangs out at Supreme
Occupation: Founder, WAH Nails

Sharmadean is an all-around stylish Brit—and MILF. Her look is inspired by sportswear, street style, Doc Martens from the '90s, and Courtney Love. In other words, she wears leather skirts and Supreme football shirts. It’s the best of both worlds.

Dresses Like: Nucky Thompson
Occupation: Fashion Director, The Rake

Catching a glimpse of Esther Quek is one of the best things about men’s shows during fashion week. Her nod to menswear is unlike anything else. For her, it’s not just about wearing any suit; she mixes classic men’s tailoring with feminine touches. Often, said suit is bright, printed, and topped off with awesome menswear accessories, such as tie bars, bow-ties, and pocket squares. You thought you looked good? Then you must’ve not seen Esther yet.

Dresses Like: David Bowie
Occupation: Style Director, Elle

Kate Lanphear is a big name in the fashion industry and is often revered as a style icon. Her punk and androgynous look has developed a cult like following—seriously, there are plenty of blogs dedicated to this woman's style. She wears tons of black, leather jackets, and has mastered the pantsuit. Her style is inimitable; New York magazine even refers to her effortless look as "the Lanphear look."

Dresses Like: Every other guy in Seattle
Occupation: Model/Actress

When we think of "tomboy style," we think of Agyness. The British model has been into masculine looks infused with her punk rock style for years. She's been known to wear vintage tees, trilby hats, and printed socks before menswear bloggers knew what they even were. Agyness has gained notoriety for her look while other models struggle to cultivate a style that's distinctly their own.

Dresses Like: A Japanese street urchin
Occupation: Designer, Hellz Bellz

Lanie is the type of woman who you take a look at twice: One because she's hot and two, her style is always on point. Her look is a mix of streetwear and comfort, and includes things like camo, baggy pants, sneakers, and plenty of beanies. And as one of the few women with a voice in streetwear culture? She's definitely the HBIC.

Dresses Like: A Scottish shepherd
Occupation: Singer

Gwen is the full package: she's talented, super hot, and has great style. Besides being the front woman of No Doubt, she also has a successful clothing line, L.A.M.B. She's evolved as an artist over the years and her style has followed suit. Her look is cleaner and more polished. But don't get it twisted, she still has a bit of tomboy in her—a tomboy who wears baggy jeans and puts on makeup.

Dresses Like: A "goth ninja" from SuperFuture
Occupation: Model

The Danish model is referred to as fashion's favorite tomboy. Her androgynous look and personal style has influenced her career—she's been known to model in androgynous photo shoots—and she's been a designer favorite since she came onto the scene in 2005.

Dresses Like: Alexander Wang's twin sister
Occupation: Blogger, Stop It Right Now

Jayne Min is that chick. Other women want to be like her and guys wish they knew her. She loves skateboarding and was the creative behind the Celine-inspired skate decks. When she's not cooking up something crazy, she's putting up awesome photoshop skills, outfit-of-the-day pictures, and style inspirations on her blog, Stop It Right Now. Her looks are minimalistic and clean but always with a mix of tomboy-slash-'90s skate-rat element to it.

Dresses Like: A cast member from Do The Right Thing
Occupation: Influencer

Are you surprised? Vashtie fits the bill: She dresses like a guy and she looks hot in dude clothes. She says she's been a tomboy all her life and describes her style as such. What separates her from the rest of the women who mix feminine and masculine styles is that she's got great taste. Let's not forget, she's also the first woman to design sneakers for Jordan brand.

Dresses Like: A '90s skater
Occupation: Model

For how pretty she is, Cara dresses like a guy more than you think. Her menswear look is influenced by street and skateboarding, and often consists of varsity jackets, beanies, graphic tees, and sneakers. Everything about her casual style says she's easy-going and laid-back—the kind of chick ideal for cuffing season.

Dresses Like: A Dior Homme mannequin
Occupation: Actress

The Twilight star is what you would call a tomboy through and through. She may wear dresses when needed, but she still favors dressing like a guy. Sometimes she even wears sneakers with her red carpet gowns.

Dresses Like: A barber shop regular
Occupation: Model, Singer

Amber is usually in tight mini dresses or equally tight leggings, but she also knows how to rock menswear-inspired looks, too. When she does, it involves sneakers, baggy pants, or good ol' Timberland boots. It's not easy to pull off something so masculine, so we respect her swag. Although, let's be honest, you could never really mistake her for a guy—from the front or back. She's has a beautiful face and, well, the assets to match.

Dresses Like: The lost member of Das Racist
Occupation: Rapper

M.I.A. has one of the most eccentric styles in the game, and it usually involves print-everything and bright colors. Believe it or not, she's also a master in menswear. She balances suits and streetwear just as well as the boys. Bad girls do it well.

Dresses Like: Downtown NYC
Occupation: Model, Blogger, Mademoiselle Kdia

Kdia doesn't dress like a guy 24/7, but when she does, her style captures downtown cool better than Opening Ceremony. Her menswear-inspired looks are hood but scream luxury—she rocks Givenchy, Céline, and Balenciaga on the reg. We call her swag "Parisian thug." It's no wonder she's Don C's lady.

Dresses Like: A British juvenile delinquent
Occupation: Singer

One of the things the Bad Boy princess is known for is her half-shaved haircut—she had, and still has, every chick out there thinking she could pull it off. But let's not forget, her personal style has also influenced a number of women. It's sexy and hood at the same time. It's a mix of streetwear and designer labels. She dresses masculine without looking butch. And for that, we salute Cassie.

Dresses Like: Big Sean in jeggings
Occupation: Singer

Ciara may wear Givenchy and Giuseppe Zanotti now, but she's still the same ATL tomboy we fell in love with while watching "Goodies." In fact, the singer will tell you herself that her personal style remains "tomboy chic." She mixes it up between Louboutins and Jordans, and looks better than us in fitted caps and baggy jeans. The best part is she looks just as hot in menswear as she does in a tight mini dress. Don't believe us? The video for her hit, "Like A Boy" is all the proof you need.

Dresses Like: Pharrell's little brother
Occupation: Singer

The 21-year-old singer was one of the first to bring back the more street look for women. She rocked Jordans, caps, camo pants, and streetwear when she first got noticed, and she’s still doing it (and doing it well) now. The only thing that’s changed is the addition of a few more Givenchy tees. It’s still up for debate whether or not others copied her style, so we’ll let you come to your own conclusion. What we do know is that Teyana has always been about this life.

Dresses Like: Kanye West
Occupation: Singer

Rihanna can do no wrong. The Barbados singer has blessed us with some of the most risqué looks, but she's also proven her style is versatile. Who else looks as hot in menswear as RiRi does? Plus, she carries herself with an attitude that screams #phuckyofashion. Her style is king—just check out her thirst-inducing Instagram.