Hailey Bieber’s Most Stylish Outfits: See All Her Best Fashion Moments

It’s impossible to talk about Hailey Bieber’s style evolution and not highlight her street style savvy. The model and Rhode beauty founder has perfectly encapsulated (and often helped usher in) the biggest fashion trends for nearly a decade. At the start of her fashion journey, that meant plenty of bomber jackets, ripped denim and ultra-short shorts paired with sky-high heels. But as Bieber’s sartorial taste continued to evolve, she enlisted the help of stylists like Maeve Reilly and, later, Dani Michelle, to help establish a more mature look that mixed oversized blazers and loafers into her favored denim and athleisure ensembles.

Born into the Baldwin family (she’s the daughter of actor Stephen Baldwin), she hit her first red carpet before the age of five. As a kid, Bieber attended movie premieres (including the 2011 premiere for her future husband Justin Bieber’s Never Say Never documentary) alongside her family. By the time she was 14, Bieber had parlayed her famous last name into a modeling career, quickly amassing a portfolio that included fashion campaigns, magazine covers and runway work.

Though she kicked off her modeling career in New York by walking for Sherri Hill in 2013, Bieber eventually became a worldwide runway regular for fashion houses like Tommy Hilfiger, Moschino, Elie Saab and Julien Macdonald. Along the way, she landed campaigns with Ralph Lauren and Tommy Hilfiger, eventually walking her last catwalk in 2018 (at Versace, no less).

From fast fashion brands like Pretty Little Thing to luxury fashion houses like Saint Laurent, Bieber’s success as a street style star has helped to make her the face of numerous campaigns, often working with multiple brands at once. In 2022 alone, Bieber debuted campaigns for Jimmy Choo, Hugo Boss, Miu Miu, Saint Laurent, Fila, Victoria’s Secret and Tiffany & Co., while simultaneously launching her skin care line, Rhode.

From her earliest red carpet days with her parents to the Met Gala with her husband (and many street style looks in between), we’ve gathered some of Bieber’s most memorable fashion moments.

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One of Bieber’s first red carpets was for the premiere of her father’s 2000 film, The Flintstones in Viva Rock Vegas, which she attended alongside her mother, Kennya Baldwin, and older sister, Alaia.

Though the Rhode founder first met Justin Bieber in 2009, she was introduced to the pop star again in 2011, when her dad took her to the Never Say Never documentary premiere in New York City.

Before working with a stylist to curate a more elevated street style wardrobe, Bieber’s looks often incorporated more casual takes on her staple pieces. Seen here in Los Angeles with Kendall Jenner, Bieber paired a white t-shirt and leather jacket with ripped jeans and Chelsea boots.

2015 was a big year for Bieber, as she landed a Ralph Lauren campaign and made her New York Fashion Week debut at the Tommy Hilfiger show. But first, she started out the year at Fendi’s New York flagship store opening in a strapless camo green number that was belted at the waist and styled minimally with nude platforms, slicked-back hair and a berry lip.

For her first Met Gala in 2015, Bieber wore a custom powder blue Topshop minidress, which included long sleeves, a mock neck and plenty of embellishment. Her clutch, strappy platforms and jewelry all matched the silver accents, and Bieber took her hair to a darker brunette shade for the occasion.

Bieber went for classic black at the premiere of the 2015 installment of Mission Impossible in New York City. Her off-the-shoulder minidress was equal parts sexy and chic when paired with strappy black heels, a slightly tousled updo and matte red lip.

While attending a gala in Los Angeles, Bieber gave her peachy pastel midi Topshop dress and glitzy Stuart Weitzman heels an unexpected twist with a vampy matte lip.

Ripped jeans were a staple in Bieber’s early street style years, as were ankle boots and leather jackets (the last of which is still a recurring component).

Neutrals may be her go-to when it comes to streetwear, but on the red carpet, Bieber is no stranger to a bold color. Case in point, this red gown that she wore to the Elton John AIDS Foundation’s annual Oscars party. The floor-length silhouette included a thigh-high slit and cut-out detailing at the midriff, and the event marked the beginning of Bieber’s partnership with stylist Maeve Reilly, who selected the model’s Nicholas Kirkwood heels.

Several months after the debut of her spring 2016 campaign with Tommy Hilfiger, Bieber wore a custom gown by the American designer to the Met Gala. Covered in black and silver sequins, the long-sleeved dress featured a thigh-high slit and open back.

The following month, Bieber took metallics to a mini length in a gold Kayat dress and matching Giuseppe Zanotti heels.

To attend a Golden Globes afterparty, Bieber chose a pink Elie Saab dress with a belted waist and a shimmering plunging neckline.

For a more high-fashion take on her preferred shorts and heels pairing, Bieber’s stylist put her in a cream look from Vera Wang consisting of an oversized sweater tucked into peplum, side-striped shorts. Sky-high Giuseppe Zanotti platforms, and a leather backpack and choker necklace completed the look.

Bieber switched up her style game at the 2017 Met Gala in a layered tulle skirt and matching bustier top by Carolina Herrera. The head-to-toe custom look also included a rhinestone-embellished netted veil by Gigi Burris and Lorraine Schwartz diamond earrings and choker necklace.

According to Maeve Reilly, Bieber had her first couture moment in Cannes at the 2017 amfAR Gala in this plum Elie Saab design. The dress was belted at the waist, with elements of velvet and chiffon. Bieber’s glam teamed matched her makeup to her ensemble with a plum smokey eye, and her long hair was styled in an undone braid with face-framing pieces.

In a more colorful street style moment, Bieber paired a yellow Michelle Mason slip dress with an embroidered Gucci bomber jacket.

Bieber’s iridescent Kaufmanfranco dress brought a bit of edge to the annual Harper’s Bazaar Icons party, thanks to distressed detailing throughout the sequined gown, plus her dark winged liner and textured ponytail beauty combo.

After New York Fashion Week, Bieber headed to London, where she was spotted in this athleisure look comprised of black Adidas biker shorts, a turtleneck and a bright orange bomber jacket.

Bieber chose a more sophisticated ensemble for the annual Hammer Museum Gala in Los Angeles, which was presented by Bottega Veneta. Naturally, the model wore Bottega Veneta for the occasion, opting for a belted midi skirt and turtleneck from the fashion house’s fall 2017 collection, which she paired with black Jimmy Choo platforms and oversized hoop earrings. She even perfectly coordinated her hair and makeup with the look, with plum liner and a sleek low ponytail tied with a black bow.

Opting for a very pink street style look, Bieber was photographed out in New York City in high-waisted, shimmering pink pants by Off-White and a matching cropped button-up shirt with wide sleeves. (A little over a year later, Off-White founder Virgil Abloh, designed Bieber’s wedding dress.)

Bieber matched her lip to her dress at the 2018 Brit Awards when she paired a dark navy lipstick with a sequined gown from the Ralph Lauren fall 2017 collection.

While co-hosting the iHeartRadio Music Awards with DJ Khaled, Bieber wore five different designer looks, ranging from a shimmery minidress to a tailored trousers and t-shirt combo. But before the show got underway, Bieber posed on the red carpet in a Zuhair Murad jumpsuit from the 2018 couture collection. The show-stopping ensemble included a plunging neckline and sheer paneling throughout, and it was embellished with sequins and fringe.

At the2018 Cannes Film Festival, Bieber’s once again coordinated with her beauty look with her dress, opting for pastel pink hair and a pink and nude Roberto Cavalli gown. The bespoke design was encrusted with crystals and fringe, and Bieber added even more sparkle with Chopard diamond earrings and bracelet.

Back to her blonde bob, Bieber hit the Billboard Music Awards red carpet in a golden Alexandre Vauthier dress. The form-fitting design featured long sleeves, a plunging neckline and a gathered twist at the center of the waistline, and Bieber kept the accessories gold, too, with Jimmy Choo platforms and Jennifer Fisher hoops.

A few weeks after getting engaged, Hailey and Justin were spotted out in New York City. Mixing feminine and masculine elements into her look, Hailey paired a floral Bec + Bridge dress with an oversized Raf Simons jacket and Alexander Wang combat boots. She accessorized with black sunglasses and custom necklaces and hoops by Jennifer Fisher (and her massive oval-cut engagement ring, of course).

A few days before she officially became Mrs. Bieber, the model was presented with the Daily Front Row’s 2018 Fashion Media Personality award by Tommy Hilfiger. Dressed in a custom green number by the designer, Bieber let the crystal-covered gown shine by keeping her accessories to a minimum.

Bieber was photographed, iced coffee in hand, on her way to the Zadig + Voltaire New York Fashion Week show in a colorful take on winter suiting. The gray checked suit was from the brand’s fall 2019 collection, and Bieber brightened up the set with an oversized, neon pink turtleneck, also from Zadig + Voltaire. White Christian Louboutin pumps matched the suit’s white plaid, and Bieber tucked her tousled waves into the back of her sweater to show off the ‘Zadig Jacket’ printed on the back of the suit.

Bieber took a break from the floor-length gowns when she attended a Golden Globes afterparty in a sequined black Saint Laurent blazer dress. The belted mini featured a plunging neckline, and was styled with Saint Laurent pumps and Tiffany & Co. diamond earrings.

To support her husband at the premiere of his YouTube docuseries, Bieber opted for a Zuhair Murad couture design from the spring 2020 collection that was fully embellished and featured a sheer skirt and ab-baring cutout.

Bieber wore a custom Versace design to the 2020 Vanity Fair Oscars Party, which included a bodysuit under sheer lace embroidered with black Swarovski crystals.

Bieber was photographed in a slew of street style looks during Paris Fashion Week, with this emerald-green skirt suit being one of the most memorable. The silk jacket and matching mini skirt were from TRE by Natalie Ratabesi, and Bieber paired the set with black and gold accessories, including Casadei over-the-knee boots, Saint Laurent sunglasses, Bottega Veneta gold triangle hoop earrings and a black Bottega Veneta Pouch Bag with gold chain strap (that BV bag would become a staple for Bieber, who seems to own one in every color).

Bieber made a strong case for winter whites when she stepped out in this neutral ensemble. She paired a cream-colored Isabel Marant coat with a white Wolford turtleneck bodysuit, high-waisted pants, Fenty boots and another Bottega Veneta Pouch Bag—this time in white.

Like the rest of us, Bieber made a face mask her staple accessory in 2020, and she adopted a much more relaxed look, too. While grocery shopping with Kendall Jenner, Bieber opted for a cozy Comme de Garçons sweater, matching knit tie-dye biker shorts and sneakers.

A few months later, Bieber traded in her leisure wear for a head-to-toe Saint Laurent look composed of latex leather leggings, a sheer polka-dotted pussy bow blouse and a leather jacket, all from the fashion house’s fall 2020 collection.

To brave the New York City cold, Bieber cozied up in an oversized Bottega Veneta teddy coat, which she dressed down with blue jeans and white Nike Air Force 1 sneakers.

Bieber wore a colorful monochromatic look while out in Paris, in a lilac knitted tank by Raf Simons and matching mini skirt by The Attico. The model coordinated her Bottega Veneta Pouch Bag with the rest of her ensemble, and also accessorized with Chanel loafers, rows of gold necklaces, gold hoop earrings, black sunglasses and a tortoise claw clip in her hair.

Another color-coordinated moment in Paris, but this time, Bieber chose a beige LaQuan Smith dress (the midriff-baring cutout drew some criticism when she wore the look to meet the President of France and his wife later that day).

By that fall, Bieber had switched stylists, turning to Karla Welch for her Met Gala look (the annual event, which typically takes place on the first Monday in May, had been postponed until September due to the Covid-19 pandemic). After teaming up with Saint Laurent for various red carpet events and street style looks, Bieber was featured as one of the faces of the brand’s denim campaign over the summer, so it wasn’t totally surprising she wore the designer at the Met Gala a few months later. Going more casual than years past, Bieber opted for a strapless black gown with a crystal-trimmed sweetheart neckline, which she accessorized with a diamond necklace from Tiffany & Co. and black Saint Laurent sunglasses.

For Elle’s annual Women In Hollywood event, Bieber’s tested out a bit of Old Hollywood in a two-piece Miu Miu set that included a high-waisted, ankle-length skirt and matching cropped blazer with an oversized white collar. She kept her accessories and makeup minimal for the occasion, opting for black Jimmy Choo pumps, Tiffany & Co. hoops and polished waves paired with a nude lip.

Bieber was back in Saint Laurent at the LACMA Art + Film Gala, this time in a structured white dress from the 2022 spring collection, complete with long sleeves and a plunging neckline (plus, the gold cuffs that were worn on the runway). Bieber, who had recently been named as a brand ambassador for Tiffany & Co., added stacks of diamond rings and a pair of diamond earrings, which she completed with a slicked back updo and matte berry lip.

Another awards show season meant another neutral was in order for Bieber, who wore a nude Saint Laurent gown with an ultra-low back and cutout detail at the waist, accentuated with a rosette, to Vanity Fair’s Oscar party in 2022. The dress was made even more dramatic, thanks to Tiffany & Co. Elsa Peretti gold cuffs and bangles.

For the 2022 Met Gala’s “Gilded Glamour” theme, Bieber and her styling team worked with Saint Laurent creative director Anthony Vaccarello on this custom white silk gown and matching feather-trimmed cape. According to Karla Welch, the design was inspired by model Jerry Hall, and “an amazing passage about a young Vanderbilt in the gilded age descending the stairs in white silk and feathers.” Bieber paired the look with sheer black tights and strappy Saint Laurent heels, plus diamond earrings and bracelets from Tiffany & Co.

A month after the Met Gala, Bieber headed to Good Morning America to promote the launch of her beauty brand, Rhode. Now working with stylist Dani Michelle on her street style looks, Bieber wore several looks throughout the day, including this Aggi black blazer from Wolf & Badger, which she paired with a black mini skirt, Bottega Veneta loafers, Balenciaga sunglasses and Tiffany & Co. jewelry.

Bieber went monochromatic for the Academy Museum Gala a few months later, from her chocolate brown hair to her custom Saint Laurent dress. The strapless design was draped and twisted at the front with a midriff-baring cutout. Bieber’s makeup (and even manicure!) coordinated with the look as well, with a square-cut, orange gemstone necklace from the Tiffany & Co. archive serving as her only pop of color.

This was the first time we saw Bieber’s new bob, but her outfit attracted nearly as much attention, with her stylist sharing that it was one of her most-liked Instagram posts. The look in question combined multiple trends, with Bieber pairing a classic Saint Laurent coat with a polo sweater (also Saint Laurent), MISBHV pleated mini skirt and Proenza Schouler loafers that were worn with sheer stockings and white socks.

Bieber added a touch of drama to a classic black dress in this custom Saint Laurent gown, thanks to a satin bow on one shoulder with a cascading split sleeve and a gloved sleeve on the opposite arm.

Though she has embraced more polished street style looks, Bieber has never entirely abandoned her preference for sportswear. While in New York City, she paired a black and blue paneled sports jacket from London-based brand Martine Rose with a gray crop top, baggy jeans, a baseball hat and square-toe loafers.

Bieber took inspiration from the ultimate Tiffany’s icon, Audrey Hepburn, to attend the reopening of the luxury jewelry house’s flagship store in New York. She wore a black Versace midi dress with an upside-down scoop neckline, and completed the look with Giuseppe Zanotti mules, a two-strand pearl necklace, pearl earrings and a Tiffany blue manicure.

Nearly a year after the U.S. launch of Rhode, Bieber brought her skin care line to the U.K., celebrating the occasion in a sequin-covered gown. The strapless silver number was part of N.21’s 2023 pre-fall collection, and Bieber went for matching gray pumps and a shimmery smokey eye.

A few months later, Bieber celebrated the one-year anniversary of Rhode in another sparkly dress—this time, a pink crystal-covered minidress from Vivienne Westwood. Once again, Bieber opted for a strapless design, but added a plunging neckline for a dramatic silhouette. And to complete the look, she chose a matching pink rhinestone bag from Cult Gaia, a pink French manicure and a diamond necklace and earrings for even more sparkle.

To introduce the newest flavor in her Rhode Peptide Lip Treatment collection — a strawberry glaze collaboration with Krispy Kreme—Bieber took a page out of Margot Robbie’s Barbie press tour handbook and dressed the part. Bieber’s first look was a strawberry-red midi dress from the Vivienne Westwood fall 2023 collection, which she accessorized with matching red-heeled mules from Maison Ernest and a rectangular Ferragamo Tote bag.

That same day, Bieber kept her red Ferragamo bag but switched outfits for an ultra-mini white Marc Jacobs dress and red Manolo Blahnik mules.

For her final launch day look, Bieber returned to red again with a strapless minidress from the Ermanno Scervino fall 2023 collection. Back in her Maison Ernest heels and Ferragamo bag, Bieber added one very important detail: strawberry earrings by Alessandra Rich.