We have witnessed many exciting waves of cultural shifts over the years regarding how women “should” and (most irritatingly) “should not” dress.
In the late 70s, the hippies did their best not to conform after an oppressive 60s. Female icons like Madonna kept the party going in the 80s by dressing and doing whatever she wanted, and then things got a bit weird in the 90s and 2000s…
… Social media boomed by 2010, and women being traditionally feminine became monotized.
The pressure was back on, and the “tomboys”, or those who wanted to self-express without judgement, cried into their baggy hoodies as they felt they were back to square one.
Thankfully, times have changed, but if you’re still not feeling very self-assured, feel free to take inspiration from these five unapologetically masculine women who are comfortable in their own skin as well as their fabulous clothes.
Kristen Stewart
Since finally breaking free of being ‘that Twilight chick’, Kristen has been flirting with the beauty of reinvention for quite some time.
Last year, her metamorphosis saw her rocking up to a red carpet premiere in nothing but men’s boxer briefs, a cropped white tank top, and a blazer that would snugly fit an American football linebacker!
And she still looked super cute.
With her typical “I’m not gonna smile if I don’t wanna” pout and her dark hair tousled as if she’d just rolled out of her bed after a drunken night on the town, this is a woman who has refined herself.
Zendaya
The leggy beauty towers over many men on the carpet; she stands proud and tall, and this year she leaned into a more masculine look.
She’s been a busy gal with a jam-packed diary, so we got to see a lot of her and her fantastic outfits on her 2025 press tour, blessing us with wide-leg trousers and crisp white shirts unbolted one button too far, like it’s a statement of intent, with neckties dangling rebelliously loose.
Zendaya is the CEO of cool, with the cuffed sleeves, letting the watch do the talking as she struts her stuff.
Chappell Roan
Call it Tomboy, call it butch-camp glamour, or whatever you label it, there is no denying she looks amazing.
With the feathered mullet, winged eyeliner, and thrifted men’s button-downs worn over glitter pasties, this woman is in a league of her own. Chappell may have piggybacked on the internet’s obsession with “masc” aesthetics and made it her own…
… or maybe we are totally off with that theory and should give her more credit for simply being herself.
She has also been known to finish a ballad in a three-piece suit and blow a kiss to the audience that feels flirtier than any ballgown ever could.
Emma D’Arcy
The House of Dragons star is the queen of her own throne when it comes to women wearing masculine clothes in royalty.
Often seen donning Carhartt jackets and Dickies pants, assembled with the quiet swagger that makes paparazzi photos look like stills from a Luca Guadagnino movie.
Emma has single-handedly made “brooding in corduroy” the mood of the year, and many of us here at Elizabeth Street have taken inspiration from this vibe.
Bailey Sarian
It seems that Bailey spends her hard-earned money on a new tattoo every week, and we are totally here for it.
Tattoos have been celebrated on men by women with daddy issues since the dawn of time, but tattoos on a chick are still a little taboo.
Girls like Bailey give off an air of “I don’t give a f**k about your taboo,” inspiring inked girls all over the world and passing the baton to less self-assured women who always fancied experimenting with body art.
Billie Eilish
Baggy Era 2.0 is somehow baggier.
And no one pulls off the loose-fitting look better than the pop star sensation, Billie Eilish.
Our favourite Billie look: basketball shorts under oversized jerseys under even bigger flannels, all paired with the dead-eyed stare that says she knows you’re already intimidated.
If I swapped my mini skirt and heels for that look, I’d feel like the ugliest woman ever, but she somehow manages to look effortlessly hot.
Every. Single. Time.
And power to her; the paradox is the entire point we are trying to make.
What These Women Have in Common
The above women may differ in their outfit styles, hair, and clothing sizes, but the one thing that unites them is their absolute refusal to perform traditional femininity.
Not that there is anything wrong with traditional femininity, but the point is a woman shouldn’t have to dress that way if she doesn’t feel like it, and that’s precisely the spirit they embody.
Their confidence is deafening.
And the best part? More and more women are copying elements of this look. The energy has officially escaped the subculture and slapped the face of the mainstream, and it looks like it’s here to stay.