Hailey Bieber’s Most Controversial Outfit Choices

Walking in heels is an acquired skill, and even the leggiest of supermodels had to start somewhere. Granted, that doesn’t excuse them from wearing flats on the runway. In 2011, a 15-year-old Hailey Bieber graced the runway for Pastry Shoes, and though the catwalk was in a mall in Las Vegas, her outfit choice was the loudest thing there. To add insult to injury, she paired the sneakers with a long-sleeved tie-dye sweater, a black sequinned miniskirt, long feather earrings, and a magenta headband. It’s every 15-year-old’s dream, but that doesn’t necessarily mean it aged well (or made sense).

Hailey Bieber isn’t afraid to admit her fashion mishaps, and she didn’t hold back when trashing her look from the 2015 premiere of “Dior & I.” During an interview with Vogue Australia, her husband Justin Bieber asked about her “biggest fashion regret.” The look in question was an oversized pink satin vest dress, with a boxy silhouette that made it appropriate for a costume party, but not a premiere: “I wore it, and I saw the photographs after and it legitimately looked like I was inside a box. I looked like a present, and it was so bad.” 

Everyone knows the number-one rule at any wedding is not to wear white unless you’re the bride. Hailey Bieber got into some hot water when she wore a Fancí Club floor-length white gown to friends Stephanie Shepherd and Larry Jackson’s wedding in June 2024. Another unspoken wedding rule is not to be too revealing or risqué, for fear of stealing attention from the couple. Once again, Bieber proved herself a rule-breaker as the dress had a gaping back cutout that put everything on display. If we were getting married, we certainly wouldn’t have been thrilled.

It is worth discussing how truly horrendous some of the outfits that Hailey and Justin Bieber have stepped out in together are — at least when paired together. In one particular instance, while Hailey was promoting Rhode in New York, she was seen in a red Ermanno Scervino strapless minidress, teamed with a coordinating bag and open-toed heels, and a silver “B” charm necklace. Justin, on the other hand, donned a gray sweatshirt and basketball shorts, a pink trucker hat, and yellow Crocs. Are we sure they were headed to the same event?

Coachella 2025 was one for the books, with Lady Gaga being one of the most highly anticipated headliners and celebrities like Julia Fox wearing iconic, albeit inappropriate, looks. What Hailey Bieber chose for the opening night of the festival, though, fell short. During the day, she wore a plain black minidress with matching flip flops, changing into a vintage Mugler leather halter top with black slacks and sneakers for that night. Bieber may prefer comfort over style for such an headline-grabbing event, but her styling was simply not up to par.

One of the most highly celebrated events in fashion is the yearly Met Gala. A-listers from all over the globe are given a theme to follow, and we get the luxury of judging the looks from home. Unfortunately for Hailey Bieber, she landed on our list of the worst-dressed celebs at the 2025 Met Gala. The theme was “Superfine: Tailoring Black Style,” and Bieber’s lack of inspiration was apparent. The entrepreneur wore a simple Saint Laurent blazer as a dress and paired it with dark stockings, platform pumps, and some Tiffany & Co. diamonds around her neck. Better luck next year, Hailey.