• Best-dressed celebrities like Oprah, Karlie Kloss, and Queen Rania embraced the summer wedding theme with elegance, color, and stylish flair.
• Fashion missteps from stars like Kim and Khloé Kardashian, Leonardo DiCaprio, and Ivanka Trump stood out for being off-theme, overly casual, or awkwardly styled.
• Public reaction highlighted a clear divide between those who nailed the dress code and those who missed the mark, sparking buzz across social media and fashion circles.

Venice, the city of love and luxury, played host to one of the most talked-about celebrity gatherings of the year. Jeff Bezos and Lauren Sánchez’s wedding celebration drew a star-studded guest list that rivaled any Hollywood premiere. But while love was in the air, fashion was the real battlefield — and not every A-lister walked away a winner.

As water taxis carried the elite across the glistening canals, cameras flashed, capturing the highs and lows of wedding-guest fashion. Some guests nailed the summery-chic dress code with effortless grace, while others left spectators scratching their heads.

Stars Who Owned the Style Scene

Oprah Winfrey kicked off the festivities in breezy summer style. Stepping into a water taxi, she wore a maroon-and-white patterned dress that was both stylish and practical for the warm Venetian evening. Side cutouts gave it a modern twist, and her angular sunglasses sealed the look with sophistication. Oprah didn’t just dress for the weather — she dressed like she owned it.

Orlando Bloom, freshly single and noticeably glowing, embraced the laid-back charm of Italian summer. His beige pants and crisp white shirt were elevated by a matching blazer, creating a look that was polished without being overdone. His buzzed haircut added a dash of rugged charm — a reminder that heartbreak hasn’t dulled his shine.

Karlie Kloss turned heads with a silky, flowing gown that looked like it belonged in a dream. The soft draped bodice hugged her figure elegantly, and the gown’s sheen shimmered under the Venetian lights. Hand-in-hand with her husband Joshua Kushner — who looked sharp in a charcoal suit — the couple radiated power and poise.

No wedding would be complete without royalty, and Queen Rania of Jordan delivered a lesson in regal refinement. Her intricately detailed gown, complete with a pink scarf and high neckline, was a masterclass in modest glamour. A delicate pink clutch in hand, she glided into the festivities like a modern-day queen — because she is one.

Usher brought a splash of retro swagger in a white, double-breasted suit straight out of the ‘70s playbook. His burgundy striped shirt, worn slightly unbuttoned, added flair, and the gold ‘U’ pendant on his necklace was a bold finishing touch. This wasn’t just an outfit — it was a statement.

Diane von Fürstenberg, the high priestess of summer elegance, wore a whimsical black dress splashed with color — pinks, blues, yellows, and florals danced across the fabric. Topped with a flowing green coat, her ensemble was the perfect blend of carefree and couture.

Ellie Goulding also embraced the festive energy. Her semi-sheer cream dress sparkled with blue sequins, and the daring cutouts added drama. Paired with a cheetah-print clutch, it was bold, sexy, and utterly summer-ready.

Even the fashion-forward Guilherme Siqueira, a Dolce & Gabbana ambassador, brought the heat. His pastel pink-and-cream suit, paired with an ornate rosary and simple white shirt, showed how to do high fashion without trying too hard.

When Fashion Fails to Impress

Unfortunately, not everyone rose to the occasion.

Kim Kardashian walked a familiar path — maybe too familiar. Her snakeskin bodycon dress clung to every curve, but it lacked imagination. With glittery straps, a lace-up bust, and pink talons to match, it was more nightclub than nuptials. And the silver sequined back clashed awkwardly with the front, leaving fashion critics baffled.

Khloé Kardashian didn’t fare much better. Her gray-on-gray look with bizarre layered textures and exposed black bra missed both elegance and cohesion. It was revealing in all the wrong ways and seemed confused about whether it wanted to be sultry or sophisticated.

Kendall Jenner played it safe, perhaps too safe. Her vintage floral Cavalli dress, halter-necked with an angel motif, was sweet but unremarkable. With minimal accessories, the look faded into the background — not what you’d expect from a fashion icon.

Ivanka Trump missed the mark twice. First with an overpriced crop-top and skirt set that looked like something you’d wear to brunch, not a billionaire’s wedding. Then she slipped into a tweed Oscar de la Renta dress with floral appliqués that screamed “bride,” not “guest.” Either way, it felt tone-deaf.

Gayle King, a Blue Origin guest like Sánchez, arrived looking ready for a grocery run instead of a wedding. Oversized green cargo pants and a basic white tee fell flat — even the denim jacket in her hand couldn’t rescue the look.

Kylie Jenner chose a gold lace bodycon dress that hugged her figure but didn’t quite fit the romantic, whimsical tone of the event. Paired with a tiny black purse and sunglasses, it came off more red carpet than wedding ceremony.

Kris Jenner leaned into drama, but maybe too far. Her voluminous black tulle gown with exaggerated sleeves looked more suited for an awards show memorial tribute than a joyful celebration in sunny Italy. Her sleek bob and dazzling earrings tried to add balance but couldn’t shift the mood.

Then came Leonardo DiCaprio, looking like he’d been dragged away from a yacht. His seersucker suit was a decent pick, but pairing it with a beige polo and his ever-present Dodgers cap ruined the ensemble. His girlfriend Vittoria Ceretti didn’t help their fashion cause either, wearing a chaotic mix of a shredded skirt, a metallic vest, and a candy-pink bag. None of it worked — together or separately.

Bill Gates, billionaire and guest of honor, put in minimal effort. His plain black suit and tie-free shirt lacked personality. Compared to the groom’s light, festive look, Gates appeared ready for a business meeting rather than a celebration of love. At least his girlfriend Paula Hurd looked elegant, even if slightly overdressed.

Even fashion legend Domenico Dolce missed the mark. A roadster-style jacket with sleeves that swallowed his arms, paired with all-black and aviators, looked heavy and brooding. Not exactly the joyful tone Venice was basking in.

And finally, Wendi Deng, Rupert Murdoch’s ex, wore a frilly brown-and-white floral number that was simply too much. Too many ruffles, too many prints, and not enough refinement.

A Wedding to Remember, Outfits We’ll Never Forget

Jeff Bezos and Lauren Sánchez hosted an unforgettable weekend filled with romance, luxury, and a parade of fashion highs and lows. For some, it was a chance to shine — to embrace the romance of Venice with flair and creativity. For others, it was a missed opportunity, lost in a sea of mismatched trends and underwhelming choices.

But one thing’s certain: everyone was watching. In a world where image is everything and weddings are no longer private affairs, each arrival on the Venetian docks became a red carpet moment — some magical, some messy, all memorable.