Celebrities With Boundary-Pushing Personal Style

Some celebrities, once they're catapulted to stardom—and the access to luxury brands and custom couture it entails—decide to take their personal style to the next level. Whether through architectural silhouettes, personal symbolism or themes, or counter-trends, the celebrities on this list never fail to break the mold, sartorially speaking. Some were ahead of their time—Björk, for example, and Erykah Badu—while present-day celebrities, like Doja Cat and Zendaya, deliberately stay ahead of the curve.

Cate Blanchett

Cate Blanchett's acting style is constantly button-pushing in the best way. As such, her style is also forward-thinking, joining eclectic and edgy sensibilities perfectly. See also: a delicate silk blouse combined with a blazer that's got the sharpest shoulders you've ever seen.

Taylor Russell

Taylor Russell started turning heads with her futuristic, surrealist fashion looks on the red carpet (particularly her promotion of Bones and All with Timothée Chalamet; this was at the Venice Film Festival). It takes impressive gumption to pull off these artitectural green pants, but she does it effortlessly.

Troye Sivan

Named on a number of "best dressed" lists, Troye Sivan has a fun approach to red carpet dressing—which just goes to show that menswear does not have to be boring. From cool colors to surprise swaths of skin (shorts and high socks!) it's daring and fun and surprising.

Hunter Schafer

Hunter Schafer has established herself as a fashion It-girl thanks to her willingness to go bold and daring (thanks in part to Law Roach). She can combine avant-garde and classic elements in a single look, like this literally windswept dress at the 2024 Golden Globes.

Timothée Chalamet

Timmy is a real treat on the red carpet. He usually leans in hard on the element of surprise, whether it be a rainboot-style rubber shoe or a gorgeous color. This is probably the moment when the fashion world sat up and took notice in this backless red outfit, designed by Haider Ackerman.

Tracee Ellis Ross

Even in her "off-duty," non-red carpet looks, Tracee Ellis Ross is giving us bold, graphic color contrast. She always looks like herself, she always looks utterly unique, and she's always experimenting—from maximalism to accessory play. If you want to spice up your wardrobe, she's your number one inspiration.

Emma Corrin

Emma Corrin regularly pushes fashion boundaries and dresses in a way that feels authentic to them—which makes it all the more interesting that their first role, as Princess Diana, was so lacy and delicate. IRL, their style just gets cooler and more forward-thinking.

Adwoa Aboah

If you like street style, Adwoa Aboah should be on your Pinterest board—she's got amazing outfit combinations that work well for everyday fashion. But, naturally, that innate sense of cool also works well on the red carpet, with creative colors and edgy silhouettes.

Florence Pugh

You never know what Florence Pugh is going to be wearing on the red carpet, and I mean that decidedly as a compliment. Sometimes she goes lacy and delicate, and sometimes (as we see here at the Met Gala) she debuts a shaved head and a tall feathery headpiece. It's always experimental!

Dua Lipa

Dua Lipa has smart and innovative style, from vintage pieces to dresses that look like chainmail. She's also got a love for the '90s and '00s with a cool girl twist; this studded Valentino trench feels like it wouldn't be out of place in one of their old collections.

Lily Gladstone

Lily Gladstone does excellent work on the red carpet, nodding to her Blackfeet and Nimíipuu heritage, often wearing Indigenous designers, and generally being the coolest person at an event. This gorgeous red sequined Valentino outfit is from the 2024 Costume Designers Guild Awards.

Billie Eilish

Like her music, Billie Eilish contains multitudes. It's alternative, it's sometimes oversized, it's vintage-inspired in places, and occasionally it's full glam. I'm always appreciative at how—even at the most red carpet events—she's dressed in exactly her signature style.

Yseult

Technically Yseult is walking a red carpet here, but! If you're not familiar with the songwriter and model, get to know her immediately. From oversized blazers and shorts, to red latex, to enormous hats and gloves, her style is bold and dramatic in the best way.

Maisie Williams

I really love what Maisie William's done with her style in the years after Game of Thrones. She experiments with cool shapes, interesting colors, and fun styling; she's kept this general vibe but has also leaned into classic and even vintage styles, including this cool plaid.

Miley Cyrus

Miley Cyrus has had a sartorial journey. The erstwhile Hannah Montana had an (age-appropriate) tween style at the start of her career, then evolved into a number of different styles—from the couture to the skin-baring. This Dolly Parton inspiration feels like a joining together of all her previous inspirations.

Jodie Turner-Smith

Model Jodie Turner-Smith has had some of the coolest red carpet looks you've ever seen. They're gorgeous, they're bold, they're usually colorful with fascinating grace notes (cobalt dress, matching gloves with long nails on them, and an oversized fascinator? Sign me up!).

Greta Lee

Greta Lee has really cool style instincts, which could take her from the sculptural to the fun and quirky. This, at the 2024 Met Gala in a favorite designer (Loewe), combines both impulses in impressive fashion, with the front architectural and the body sheer and playful.

Lil Nas X

Lil Nas X is incredibly playful with his red carpet fashion (including attending one Met Gala as a bedazzled cat, no big deal). While plenty of male celebs have shown up in kilts and skirts, Nas is regularly turning up in a full ball gown and plenty of sparkle.

Chloe Sevigny

Chloe Sevigny has been marching to the beat of her own fashion drum since the '90s. Back in the day, she was the definition of cool New York girl fashion, and in her more mature iteration, she's still pushing buttons and making unexpected couture choices.

Zendaya

Zendaya knows about style (and, in her work with Law Roach, has made a lot of cool red carpet choices). From selecting the perfect vintage piece to attending the 2018 Met Gala in a feminized suit of armor—channeling Joan of Arc, naturally—it's history-making.

Fan Bingbing

Chinese actor Fan Bingbing has big, bold, colorful style. This is at the 2023 Cannes Film Festival, which is honestly her perfect fashion milieu—it's the opportunity to break out a long, gorgeous dress in a vivid color. She wears the heck out of flamboyance.

Cardi B

An inimitable combination of couture, avant-garde, and button-pushing, Cardi B is often imitated but never duplicated. She's been daring, she's been delicate, she's gone to the Met Gala with a train so big it required multiple handlers—more than once!

Lady Gaga

While Lady Gaga might not be breaking the internet with a meat dress nowadays, she's still tapped into her iconoclast roots. This is at the 2024 premiere of the TV special Gaga Chromatica Ball, she's literally wearing a Selva outfit that's made partially from car parts.

Janelle Monáe

While Janelle Monáe often defaults to a black and white color scheme that plays with dimension, color, and shape, she'll still give us a color moment from time to time that's still in keeping with her style. This is Glastonbury Festival 2024, and it's honestly perfect for an outdoor festival.

Aishwarya Rai 

Aishwarya Rai Bachchan has an elegant red carpet style that nevertheless dares to play with volume and color; she often nods to her Indian heritage through the designers she wears or colors she favors. Here attending Kinds Of Kindness at the 2024 Cannes Film Festival, it's the perfect venue for her.

Elena Lenina

If you're not familiar with Elena Lenina, who's a Russian TV personality and actor, she's one of the attendees at the Cannes Film Festival (this is 2021) with the most over-the-top style. Maybe it's the feet-high hair, maybe it's the "chains" on her dress, but this might be her biggest moment? Which is really saying something.

Doja Cat

If you've ever heard of the notion "anti-fashion," Doja Cat embodies it: she wears what she likes, regardless of any kind of trend. Here attending the 2024 Annual Fashion Los Angeles Awards, her furry coat over sheer lingerie was capped off with oversized glasses and a literal suitcase with clothes spilling out.

Rihanna and A$AP Rocky

You could put either Rihanna or A$AP Rocky on this list individually, because they both favor a bold and high-fashion look. But their appearances on the red carpet together—often in complementary or matching outfits—have taken their couture looks to new heights.

Beyoncé

Beyoncé has come a long way from her start in Destiny's Child. Her gorgeous, edgy performance style is where we see a lot of her creativity; during her Renaissance tour, she even encouraged fans to dress in their best silver outfits so as to create a "shimmering human disco ball each night."

Erykah Badu

Since the '90s, Erykah Badu's neo-soul, Afrofuturistic style was ahead of its time—including wearing headwraps on the red carpet that became a symbol of Black femininity and was a completely different aesthetic than that of her contemporaries. This, at the 2024 Met Gala, is a modern iteration of her classic look.

Tilda Swinton

Few people are more surprising on the red carpet than Tilda Swinton—and she's rarely, if ever, following a trend. Her look is sometimes androgynous, sometimes bold and maximalist (as we see here at The Twenty Two party in 2022), often eclectic, and never, ever boring.

Björk

The queen of the unconventional look, Björk's style goes there in every sense of the word. This sculptural 2023 Coachella look is about par for the course, but I will never, ever forget the time she went to the Oscars wearing a swan dress (in absolute defiance of the black tie dress code), shocking every single person at home and at the ceremony. Iconic!