Even when she was a tween, Hailey Bieber knew a good outfit when she saw one.
“I remember watching ‘Hannah Montana’ and being so inspired by Miley [Cyrus]’s fashion on the show, and wanting to recreate the outfits and put my own spin on them,” said the model, Rhode founder and 2026 WWD Style Awards Style Trailblazer honoree.
This was, of course, years before Bieber would launch her modeling career; become the unofficial poster girl of Gen-Z style; debut a generation-defining beauty brand — and then sell it three years later for $1 billion to E.l.f. Beauty — all while inaugurating (if, at times, inadvertently) several additions to the beauty lexicon, including but not limited to: strawberry girl makeup; glazed doughnut skin (and its subsequent offshoot, glazed doughnut nails), and even chocolate syrup hair, as one viral Vogue article described Bieber’s 2024 transition to brown locks.
Is she ever surprised at which of her style choices the internet fixates on?
“Definitely,” said Bieber. “It’s always surprising to me what things kind of take off, but I think it’s really cool to be able to put something out into the world that resonates with people.”
Besides, far be it from her to deny the people a little whimsy.
“It brings people together when you all gravitate toward something similar. With all of those names — like strawberry makeup and latte makeup — social media has created a space for people to play and to have a little bit more fun with self-expression and makeup, and I love that,” she said.
Indeed, play is also part of the formula when Bieber, who works with stylists Dani Michelle and Andrew Mukamal, thinks about the art of dressing.
“When I feel good in clothes, is when I feel they look the best — a lot of it comes from the inside-out,” she said, adding, “one thing I’m always aiming for is to be effortless and chic, and like I’m wearing the clothes and not that they’re wearing me.”
Hailey Bieber’s street style.
Aeon/GC Images
There’s also the matter of caring for her now 16-month-old son, Jack, whose own play Bieber also now takes into account when outfit-planning. “He’s kind of getting into toddler territory, where their hands are dirty and sticky, so I like to wear things that make me feel good but that I can also really ‘life’ in,” she said.
Pieces that stay heavy in the rotation include cozy-yet-stylish sweats (“The Row makes really yummy, chic sweatpants,” said Bieber); oversized hoodies from husband Justin Bieber’s apparel line, Skylrk; white Ts (you know, ones that make cheeky reference to “nepo baby” discourse and ones that don’t) and, Mrs. Bieber’s favorite: statement outerwear.
Hailey Bieber in Saint Laurent at Paris Fashion Week.
Stephane Cardinale – Corbis/Corbis via Getty Images
“For me, the coat or the jacket, a lot of the time, is the focal point,” she said. “I always find it difficult in the summertime where it’s like, ‘I can’t wear a jacket — what can I make of this outfit?’ That’s when I’ll usually lean towards something easy, like baggy linen pants and a tank top.”
She added that her style icons through the years have ranged from Rosie Huntington-Whiteley to Rihanna to Kate Moss and Princess Diana and beyond.
“I’m very inspired by the era that was the ‘90s — there was just this sense of cool effortlessness,” said Bieber, whose latest Valentine’s Day campaign for Victoria’s Secret happened to include a playful recreation of a 2001 catalog ad featuring Gisele Bündchen painting her toenails from the bottom drawer of a bureau.
A summer SoHo, New York outing.
TheStewartofNY/GC Images
“Gisele is just a forever reference — when you think of Victoria’s Secret, you think of her and the amazing Angels, so that was fun and felt very bombshell and sexy,” said Bieber, who also fronts JPMorgan’s Chase Sapphire Reserve credit card, and last summer became the global face of DKNY.
During her teen years, Bieber entered the world of runway modeling for a period, walking during fashion weeks for houses such as Versace and Off-White, whose late founder, Virgil Abloh, also designed her 2019 wedding dress and ultra-long veil, which famously read ”Till death do us part” in bold lettering.
“I had good experiences with runway, but it was also hard for me because I was not very tall, and people made it seem that there’s a certain criteria that has to be met to do runway, and to do it well. That was tough because I didn’t feel that I belonged on the runway very much,” said Bieber.
Hailey Bieber last September in New York.
The Hapa Blonde/GC Images
Since stepping away from the catwalk, though, Bieber has managed to turn everyday moments — and not-so-everyday moments, for instance ringing the New York Stock Exchange opening bell last September to celebrate Rhode’s E.l.f. Acquisition — into standout style affairs.
“The skirt suit I wore that day was one of my favorite things that I wore last year,” said Bieber of the Calvin Klein black pinstripe wool ensemble she donned to the ceremony, which coincided with Rhode’s record-breaking retail debut with Sephora. “When we rang the bell, I felt like [the suit] was so chic, but also a little bit sexy, and very powerful. And when I think of power dressing, that’s what I lean toward most, is suiting and jackets. That feels very boss to me.”
As for what she’s most looking forward to experimenting with next?
“For me, it’s easy to feel safe in things that are monochromatic, or all-black or beige and brown tones that I know work for me, but I definitely would love to continue to play around with that a little bit more with color, silhouettes and textures,” Bieber said.
