Hailey Bieber is a supermodel-in-the-making. Here, the It girl heads to Brooklyn in the season’s chicest tomboy-inspired looks.

Portrait of Tammy Strobel

Hailey Bieber is a supermodel-in-the-making. Here, the It girl heads to Brooklyn in the season’s chicest tomboy-inspired looks.

Cardigan, Tommy Icons. Dress; scarf (in hair), Hilfiger Collection. Sports bra, Tommy Jeans. Bracelet, Cartier

It’s late summer in Brooklyn, and two 20-somethings, a woman and a man, have halted at an intersection. The woman squints, processing. The man has a momentarily confused look on his face. The woman proceeds to do that thing that people do when they’re feigning discretion while also trying to get a point across. She holds her hand up to her mouth, palm flattened, and exaggeratedly asks, “Is that Hailey Baldwin?” 

Indeed, it is Hailey Baldwin—now Hailey Bieber—posing on the sidewalk in hip-highlighting briefs. Bieber, who recently turned 22, knows something of fame. Her father is actor Stephen Baldwin, her uncle is Alec, and her Brazilian-born mother, Kennya, is the daughter of a Grammy-winning composer. But now Bieber herself is becoming universally recognised. The starstruck pair on the corner weren’t the only passers-by who froze. 

My Reading Room

T-shirt; bikini top;bottoms; sunglasses; socks, Emporio Armani. Scarf (in hair), Hilfiger Collection. Bandana (worn as bracelet), Saint Laurent by Anthony Vaccarello. Jewellery (worn throughout): Earrings, De Beers. Necklaces, Jennifer Fisher and Van Cleef & Arpels. Bracelets, Cartier, David Yurman and Phillip Gavriel Fine Jewelry. Ring, Roberto Coin. Watch, Rolex. Slippers, stylist’s own

“Over the past year,” says Bieber, sitting in the passenger seat of an RV that has served as her dressing room for the day, “I’ve had more attention on me than I’ve ever had in my life. Even before… ” Here she pauses. It is not an insignificant pause. She is taking a moment because the “before” alludes to the time leading up to her engagement to singer-slash-millennial deity Justin Bieber, which occurred in July last year. 

My Reading Room

Jacket; swimsuit; foulard; sneakers, Versace. Bike shorts, American Apparel. Scarf (in hair), Hilfiger Collection. Socks, Tommy Hilfiger.

Understandably, that news propelled her further into the limelight. And, also understandably, she wants to keep quiet about it. But, as she was saying, her profile was skyrocketing before the ring: She has been hosting (along with rapper and actor Method Man) celebrity rap-battle show Drop the Mic since 2017; she was named a global brand ambassador for Tommy Hilfiger last spring; she has walked coveted runways in recent seasons (including Moschino and Versace); and she is tight with the glitteriest of this generation’s glitterati—Jenners, Hadids, et al.

My Reading Room

Hoodie, swimsuit; bikini bottom; hat; sneakers, Fendi

Bieber says that with her career kicking into overdrive—and her romantic life having provided one of the past year’s biggest pop-culture headlines—she has come to learn the importance of taking time to recharge. “It’s easy to not think about your mental health or your physical health because you just keep pushing, pushing, pushing. Before last year, I wasn’t balancing anything.” Her outlet for maintaining an equilibrium? Church (“I actually listen to sermons on my phone when I’m on the road”), boxing classes (“as a New Yorker, I’m a bit aggressive sometimes”) and her family (“they’re not afraid to call me out on my stuff”).

My Reading Room

Cardigan; top; swim bottoms; jeans; bag; headband; phone case, Chanel. Visor, adidas. Scarf (in hair), Hilfiger Collection

Bieber has also become a style phenomenon. If Bella Hadid and Kendall Jenner have maxed out on the slickened Internet-girl trend, Bieber’s leanings are a little punchier and a little more tomboyish. Her his-and-hers looks with her husband are indicative of this. For example, one paparazzo snap of him in a Supreme tee and her in a college sweatshirt made the rounds a few months ago. Those complementary outfits struck a chord of easy, hyper-casual, graphic-chic that seems to be gaining speed industry wide. “I’m obsessed with big, clunky leather jackets. One of my favourites is a men’s Balenciaga piece,” she says, “I’ve always thought there was something really fun about a lanky girl in very boyish clothing. I love dresses with sneakers.” 

My Reading Room

Jacket; top; shorts; bag; socks, Louis Vuitton. Bike shorts, T by Alexander Wang. Hat, ’47

Bieber’s offhand effortlessness in the way she examines self-presentation runs from her most memorable ensemble ever worn on a catwalk—“a tiny, nothing little slipdress” at Alberta Ferretti—to her tattoos, which are delicate and unobtrusive. Her latest is a faint heart, on her collarbone. “I want more,” she says, “but I’m keeping space for my kids’ names and certain sentimental things, and I don’t want to fill all the cute spots before… I get there.” 

Despite the hectic pace of her current life, Bieber seems to have found a satisfactory rhythm. And, with that rhythm, happiness. Her demeanour, at the end of a long day is serene. She’s not in any manner rushed. Upon hearing a final congratulations, she smiles widely. “[Justin] is incredible. He crushes everything. Every song, every feature. It’s crazy to see what he does. I’m always blown away,” she says.

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Photographed by Zoey Grossman. 

Styled by Miguel Enamorado

Makeup: Cyndle K using Chanel Beauty

Hair: Joey George 

Manicure: Dawn Sterling/NailGlam Productions Production: Alex Zsebik/Kranky P roduktions