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Hailey Bieber’s Fashion Moments Ranked

Olivia Di Pede

September 12, 2019

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Aside from her connection to Justin Bieber, Hailey Bieber has also carved out a huge name for herself in the world of fashion and modeling. Her street style sparks trends worldwide and her sparkling red carpet moments are almost always swoon-worthy. Follow along as we rank some of her most memorable fashion moments and whether she nailed the look or missed the mark.

23. Nailed It: Vanity Fair Oscar Party 2018

Hailey looked absolutely gorgeous when she stepped out in 2018 at the Vanity Fair Oscar Party. We love the detail of this dramatic silver number that featured a subtle pattern along the skirt and intricate draping on the chest and bodice.

Photo by Dia Dipasupil/Getty Images

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22. Missed The Mark: Balmain and Olivier Rousteing 2016

We have to admit we weren’t huge fans of this look that Hailey wore to a Balmain and Olivier Rousteing event in 2016. The blush corset-style dress and over-the-knee boots didn’t seem to balance each other out well and the combination of the pastel coloring was a little questionable.

(Photo by Paul Zimmerman/Getty Images)

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21. Nailed It: Met Gala 2019

Hailey’s look for the 2019 Met Gala definitely made heads turn for all the right reasons. The soft pink color worked fabulously with her tanned skin and platinum tresses. The low back detail added something eye-catching and the black bow in her hair completed the look by adding a feminine flair.

(Photo by Karwai Tang/Getty Images)

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20. Missed The Mark: “Americans In Paris” Cocktail Party 2019

Hailey somewhat missed the mark with this bright yellow look she wore to the Americans In Paris cocktail party in 2019. While we love the neon color of this minidress, the shape simply wasn’t the most flattering and seemed to drown her figure.

(Photo by Marc Piasecki/Getty Images)

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19. Nailed It: Turner Upfront Event 2018

Hailey Bieber showed off her rose-tinted locks in a super strategic way at the 2018 Turner Upfront Event in New York. She rocked a chic blazer dress which featured a plunging neckline and a chunky belt tied around her waist. Her choice to wear all black was perfect because it allowed her pink locks to truly shine and steal the show without having to compete with any other colors.

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18. Missed the Mark: Whitney Gala 2018

We are huge fans of leather, especially for a glamorous gala, but the leather look that Hailey wore to the Whitney Gala in 2018 seemed to miss the mark. While the shape of this dress is certainly flattering to accentuate her figure, the texture of leather came across a little overly shiny and tacky.

(Photo by Dimitrios Kambouris/Getty Images for The Whitney Museum of American Art)

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17. Nailed It: Tiffany & Co. Event 2016

Hailey definitely has a penchant for subtle sequins and glitz when it comes to fashion, and this dress she wore to a Tiffany & Co. event in 2016 is the perfect example of that. She stepped out wearing a dainty powder blue dress that featured a strapless neckline and a bodycon shape. The dress truly showed off Bieber’s trim figure and her choice of wearing silver metallic shoes highlighted the soft glitter detailing of her dress.

Photo by Dennis van Tine/ABACAPRESS.COM

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16. Missed The Mark: Fashion Awards 2017

While it’s hard to go wrong with a simple little black dress, Hailey managed to do so at the 2017 Fashion Awards. The dress itself is quite safe and simple, however, as one of fashion’s leading ladies, we definitely had higher expectations for her look at the event.

(Photo by Jeff Spicer/BFC/Getty Images)

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15. Nailed It: Cannes Film Festival 2017

Hailey Bieber is no newbie when it comes to the Cannes Film Festival and has made quite a few appearances over the years at the glitzy red carpet event. In 2017 she stepped out wearing this geometric white number that featured a flared skirt and ultra-high slit. The crisp white look made her sunkissed skin pop and the sparkling embellishment on the bodice added a glam factor.

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14. Missed The Mark: Pretty Little Thing x Hailey Baldwin Event 2018

Hailey stepped out at the launch event for her collaboration with Pretty Little Thing wearing a silver sparkling suit. While we absolutely love the plunging neckline and belted waist of the glitzy blazer, the wide-leg pants could have used some final adjustments at the tailor to fit her perfectly.

(Photo by Gregg DeGuire/Getty Images)

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13. Nailed It: amfAR Gala 2017

Hailey’s sartorial red carpet choices typically involve slits, glitter, and sheer paneling, so this look she wore for the 2017 amfAR gala was definitely quite unexpected! The velvet detailing and royal purple color brought a luxe feel to her outfit, while the sheer paneling and embellishment along the waist made the entire look appear a little more soft and feminine. She topped her look with a messy bun and smokey purple lids.

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12. Missed The Mark: NBA Awards 2017

Hailey had an unfortunate fashion miss at the 2017 NBA awards where she stepped out wearing this metallic black and gold look. The gold seemed to give off a green tinge that we weren’t the biggest fans of, especially in combination with the abstract mesh pattern.

(Photo by Jamie McCarthy/Getty Images for TNT)

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11. Nailed It: Billboard Music Awards 2018

Hailey stepped out for the 2018 Billboard Music Awards wearing a sultry shimmering dress that definitely turned a few heads. The champagne number featured a dramatic twist detail along the waist and a plunging neckline. The revealing look was balanced out by the long sleeves and floor-sweeping skirt. We love how this look flatters the golden tones of her skin and hair!

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10. Missed The Mark: Tribeca Film Festival 2018

We love a lady in red, but we weren’t the biggest fans of this red fringe dress that Hailey wore to the Tribeca Film Festival in 2018. The look almost seemed more appropriate as a dance costume with all the fringe, lace and sheer detailing!

(Photo by Mike Coppola/Getty Images for Tribeca Film Festival)

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9. Nailed It: TAO, Beauty & Essex, Avenue and Luchini Grand Opening 2017

In 2017, Hailey stepped out at a grand opening event wearing this chic and glam mini dress. Silver sparkles have been her go-to over the years but we especially love the flattering neckline and long sleeve detailing of this look. She showed off her décolletage by pulling her tousled blonde locks up into a messy ponytail and finished the look with a pair of oversized hoops.

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8. Missed The Mark: The Art of Elysium 2017

As much as we love this bright tangerine color on Hailey, we have to admit that there seemed to be a little too much going on with this dress she wore to an event in 2017. From the feathers to the cutouts to the bright color, we didn’t know where to look!

(Photo by C Flanigan/Getty Images)

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7. Nailed It: Maxim Hot 100 Party 2017

Bieber is clearly a fan of minidresses, and rightfully so with the lean, long legs she has! For the 2017 Maxim Hot 100 Party, she rocked a long-sleeve white mini dress which featured a glamorous train trailing down one side of her leg. The look was the perfect flirty option for a nighttime event and we love the youthful half-pony she added to her tousled blonde waves.

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6. Missed The Mark: Hammer Museum 15th Annual Gala 2017

Hailey definitely looked super classy at the Hammer Museum 15th Annual Gala in 2017, however, we felt this ensemble didn’t ring true to her personal style. Typically Hailey wears something a little edgy or sporty, but this look seemed overly modest and professional. We could definitely imagine something like this in Meghan Markle’s wardrobe, however, it came as quite unexpected from Hailey.

(Photo by Donato Sardella/Getty Images for Hammer Museum)

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5. Nailed It: VMA Awards 2017

This jumpsuit fashion moment from the 2017 VMA’s was undeniably one of Hailey’s most memorable looks! We love the sheer, embellished detailing that showed a little skin in the most glamorous way possible. The glittering look emphasized her ultra long legs and the chunky sash around her waist really showed off her tiny waist. Her platinum locks fell wispy and straight behind her back and her makeup was bronze and glam.

Photo by John Salangsang/BFA/REX/Shutterstock

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4. Missed The Mark: Polo Ralph Lauren Fashion Show 2014

There’s a time and place for flannel, but we’re just not sure it’s at a fashion show. We can definitely appreciate how Hailey styled this flannel shirt with leather for an edgy twist, but it came across as a little much, especially with a belt slung around her hips.

(Photo by Craig Barritt/Getty Images)

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3. Nailed It: Met Gala 2018

Hailey Bieber wowed at the 2018 Met Gala where she stepped out in this smokey grey floor-sweeping number! She looked completely angelic in the chiffon Tommy Hilfiger dress which featured draped off-the-shoulder sleeves and a flowing skirt. To highlight her rose-tinted lob, Bieber ornamented her head with a variety of white flowers and crystals which added a feminine and boho feel to her Met look.

Photo by Lionel Hahn/ABACAPRESS.COM

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2. Missed The Mark: bareMinerals’ Global Wellness Retreat 2018

We love a good blazer moment on Hailey, but this look she wore to the bareMinerals’ Global Wellness Retreat in 2018 wasn’t one of her better ones. The look felt oversized and messy, rather than the polished and effortless vibe we usually get when she steps out wearing a chic blazer.

(Photo by David M. Benett/Dave Benett/Getty Images for bareMinerals)

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1. Nailed It: Cannes Film Festival 2018

Of all of Hailey’s swoon-worthy fashion moments, our favorite has got to be the glittering blush dress she wore to the Cannes Film Festival in 2018. The look was very reminiscent of the dress Marilyn Monroe wore for her “Hello Mr. President” song with its sheer champagne color and crystal embellishment throughout. We especially love the soft floral detailing along the bust of the dress which highlights her rose-tinted tresses flawlessly.

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Olivia Di Pede

Olivia loves all things fashion, beauty, and entertainment. In her free time, she can be found taking yoga classes, reading thriller novels, and styling outfits on Instagram.