The Most Questionably Dressed Celebs at Lauren Sánchez and Jeff Bezos’ Wedding Weekend

Kylie Jenner arrived at the wedding looking like she confused the event for a Fembot premiere. She showed up in a shiny silver corset gown that flirted a little too closely with bridal white and broke the first universal rule of what not to wear at a wedding: Never wear white and never try to upstage the bride, especially not by looking like an overly ambitious bridesmaid trying to manifest a wedding. The styling vision behind the lace-up detail that started at the bust and ran dramatically down to the floor remains a mystery, and the corset was cinched so tightly it looked like her ribs were struggling. While everyone else channeled elegance, Jenner gave us a sexy tube of aluminum foil.

Considering how hard it is to find something Sydney Sweeney doesn’t look good in, we’re starting to think this was an intentional sabotage attempt by her stylist. Spotted at Hotel Gritti ahead of the island wedding, this pre-wedding look was hard to defend. The ruffled shorts looked like grandma’s bloomers, the cinched waist did nothing for her figure, and the styling felt like an afterthought. It almost looks like she borrowed it from the hotel lost-and-found. Unfortunately, it’s just another entry in Sydney Sweeney’s growing collection of inappropriate wedding guest looks that turned heads.

It feels awfully wrong for the bride to land on the worst-dressed list at her own wedding, but we couldn’t just overlook Lauren Sánchez’s stiff dress fail. The gown had an ambitious design: floral embroidery, shiny bodice, and a dramatic silhouette, but they just didn’t work well together. Sánchez’s other wedding looks were elegant, but this one felt like a misstep.

Model Brooks Nader showed up looking like she was headed to a poolside photo shoot, not a billionaire wedding. The soft, romantic pink was undeniably lovely, but that’s where the compliments end. The dress itself was shapeless and did nothing for her figure. We might have overlooked the extreme cleavage situation if the final result had been stunning, but the overall effect sacrificed comfort for a gown that didn’t deserve it. Nader’s tousled hair and rosy glow were doing all the heavy lifting, and everything else was barely hanging on.

Kim Kardashian arrived at the hotel ahead of Lauren Sánchez and Jeff Bezos’s wedding, looking less like a guest and more like Bianca Censori. We’re used to the socialite showing skin in cleavage-baring and body-hugging outfits, but this time, the tailoring didn’t suit her, and it seemed like she was trying too hard. The black was faded, the bandeau looked more like a stretched-out tube sock, and the hems were curling like they’d survived a few too many spin cycles. Her Balenciaga waistband peeked out like a desperate label grab, and the wraparound sunglasses felt like the most expensive part of the outfit. Even a dollar-store bikini would’ve looked crisper.

Oprah Winfrey showed up in a rose-toned gown that was wedding-appropriate, but overwhelmed by ruffles, pleats, and sheer sleeves that didn’t do her any favors. The silhouette drowned her frame, and the styling missed that sharp, powerful elegance we know Oprah can pull off with ease. It isn’t the worst we’ve seen from Oprah, but we definitely expected better.