A female who wears clothing that corresponds to her own ideas of style tends to be very alluring and draws attention without trying. She has no problems about what she wears or who has thought they are the current trend. For centuries, fashion has sought to create rigid definitions for women’s clothing, but every so often, some of our iconic female figures graciously break out of these traditional definitions and express themselves in ways that challenge the norms, like wearing large men’s pants with an expression that says, ‘I dare you to challenge me!’
In 2026, tomboy style isn’t a phase, the cultural shakeup of a lifetime, complete with nothing short of a rebellion or six-month shelf life (though we’ll probably call it something different; how about a Tiktok aesthetic). This is truly a full on cultural reset that has been coming for quite some time now. And these women have been at the forefront of this ‘movement’ for as long as we’ve been having trends; therefore, as a final thought…here we go…
Why Tomboy Style Is Having Its Biggest Moment Yet
Prior to viewing the icons, let’s quickly discuss the fact that designers like Celine are currently featuring androgynous cuts in various ways within their collections and that women in sharp-shouldered suits are now consistently outshining everyone else on the red carpet, usually wearing a dress (and that every year during September there is a spike in Pinterest searches for “tomboy jeans,” as well as a growing trend among Gen Z where they build an entire wardrobe based on the idea that clothing is not meant to be worn by either sex). These are now being increasingly reserved for today’s women, some of whom have been creating/filling this cultural gap for several years whether they realize it or not.
Robyn Rihanna Fenty has completely transformed the definition of what constitutes as beautiful (what women can be perceived as beautiful), but what sets her apart and makes her so intriguing is not only that she absolutely refuses to be put into a box (e.g., either a tomboyish or feminine style), but she now simply calls herself by her own name and does what makes her happy instead.
The Baggy Jeans Era Nobody Talks About Enough
Before creating her successful Fenty brand, Rihanna was already known for her relaxed style of baggy pants, work boots, T-shirts with pictures on them and scarves around her head , all of which attracted lots of attention with how naturally cool she looked in them. The way she put together casual outfits did not feel overly fussy or made up; they just felt very real/true to herself. Even now, all these years later (2026), there continue to be very popular Pinterest boards dedicated to those same types of casual outfits from some of the earliest pictures taken of Rihanna.
Rihanna at the 2025 CFDA Awards
Rihanna attended the 2025 CFDA Fashion Awards wearing a contemporary version of an Alaïa zoot suit, calling it “postpartum-forward” , possibly Rihanna’s greatest catchphrase. She was absolutely correct! The look was edgy, genderless and gorgeously fashioned. The same woman arrived at the Dior Haute Couture show wearing a black puffer coat, newsboy cap and coordinating skirt , all tomboy-inspired pieces that she turned into the most discussed look of the week, despite the design having nothing to do with her tomboy-like demeanor.
Rihanna is living proof that being tomboy is not about “dressing down.” It’s about possessing such a firmly defined identity that the clothing you wear , no matter where they originated , follow along with who you are as a person.
Billie Eilish may be the most scrutinized person in pop culture when it comes to clothing decisions. For the first part of her career, Billie wore intentionally oversized (gigantic sweaters, shorts that were way too big, and blazer-like jackets), which earned her praise as an icon of body positivity while others criticized her as not feminine enough. When she began wearing more fitted style choices, she was accused of selling out.
Having so many people voicing their thoughts on Billie’s fashions is, in fact, one of the greatest compliments that she could receive.
The OG Streetwear Era
Billie’s first appearance was based on streetwear from the past. Examples would include her neon hair, large Gucci shirts, Chrome Hearts jackets, Nike shoes and Jordan apparel. She wore basketball shorts and had knee pads on stage when performing. She seems to have borrowed clothes from a trendy teenage male and turned them into her unique look. Gen Z went crazy when they saw her.
The “Chic Tomboy” Era
Billie entered a stylistic phase that fashion critics called “chic tomboy” starting in 2024 and continuing through 2025. Examples include a Chanel tweed blazer worn with wide-leg pants; a two-tone, sailor-inspired Prada suit worn to the Grammys; and a pinstripe baggy-style suit with soft brown hair. For award shows, she is still not wearing bodycon dresses, nor does she need to, as she has developed her entire image from the standpoint that you do not have to dress according to feminine performance standards if you do not feel like doing so.
Her partnership with Nike has been one of the most highly sought-after collaborations in the streetwear world over the last decade. The fact that she has also earned two Oscars while being herself reflects that energy.
Rita Ora
As Rita Ora pointed out in an interview with Vogue, “I don’t really wear dresses that often, so I tend to add some tomboy pieces to my wardrobe.” She also stated to The Daily Front Row, that her must-haves would be “very good jeans, a plain white t-shirt, and a good pair of trainers.” Plus she claimed that “I am a tomboy at heart.”
At the 2024 Fashion Awards in London, Rita wore an oversized, customized grey blazer from Primark; a pinstriped shirt; and a polka dot salmon tie; while exhibiting bleached eyebrows, chunky stacked rings, and a mullet cut (also colored bleached).
Rita’s 2024 Fashion Awards Look
There is no denying that it was one of the most influential looks of the year in terms of fashion. The combination of the grey suit, punk-rock accessories, and mullet is best described as the collision of ’80s power dressing with downtown garage band style. Even Bebe Rexha commented on it asking if Rita Campbell would be releasing a rock album to go with that look, which just goes to show how much attention this outfit received.
Additionally, Rita’s hairstyle generated a lot of buzz about what hairstyles will be popular in 2025. And Rita’s outfit was from Primark! She took a high-street suit and made it the most talked-about look at a major fashion event. Iconic behaviour.
Rita’s ability to swing between ultra-glamour and ultra-androgynous has always amazed me; one day she can show up to a red carpet wearing a couture gown, the next day she walks out of her house head-to-toe in denim. She doesn’t just fit into a single category; she owns the entire street.
The New Wave: Who’s Defining Tomboy Style in 2026
The influence of this group of icons mentioned above had created something that was only a beginning of what would come next. Ayo Edebiri has made an impact on red carpets everywhere with her style as she wore sharp tailoring at all times which seemed not only easy to wear but also super cool as well! Doechii is pushing boundaries with their fire uniforms that are so avant-garde that one could almost say they are no longer dressed as a person but rather as a work of art. Janelle Monáe has been doing her thing for years now far before the majority of today’s “fashionistas” were even contemplating becoming one.
Now let’s talk about how we see culturally without the actual terminology attached…There are oversized blazers being worn over nothing at this point…then there is cargo styling coming back and straight legged jeans with loafers & tee shirts are the “unofficial” standard uniform of every city globally today. We can also see tomboyish styles everywhere as well even though they may not be called by that name.
What These Icons Have In Common
All these women have one thing in common; it’s not the same item of clothing; it doesn’t even share the same silhouette. The only thing they share in common is that none of them are dressing for someone else’s aesthetic approval.
For example, Rihanna goes to the farmer’s market in oversized denim and a graphic t-shirt, and she still outshines everyone at any gala. Billie Eilish walks out in basketball shorts and knee pads in front of millions on a concert stage and wins fashion awards for these looks. Rita Ora shows up in a Primark suits to the biggest fashion night in the UK and makes it feel like it was the most intentional and well thought out choice to be made by anyone in the whole room.
Real tomboy style has never been a costume, and it has never been an aesthetics that is displayed for your Instagram followers, instead real tomboy style has always been a real relationship with the clothing you own that begins and ends at you. There are no rules; there are no dress codes, and you never have to explain yourself to anyone.
Now it is the year 2026, and fashion continues to reject the idea that a woman must dress a certain way because she is a woman, none of these women look ahead of their time to me; they look like they belong here.
