The best and worst outfits billionaires have worn in 2025 so far

Business Insider

a day ago

Jeff Bezos and Taylor Swift are among the billionaires with sharp style moments this year.
A mix of diamond jewelry and strong silhouettes has enhanced their looks.
Others, however, have missed the mark with some of their fashion choices.
Billionaires like Jeff Bezos and Taylor Swift have been everywhere this year. That includes this fashion list.
They're both among the wealthy figures who have shown their riches in stunning diamonds and standout outfits on red carpets this year.
Other billionaires are on this list for another reason: Their fashion has missed the mark at one point or another in 2025.
Here's a look at the best and worst outfits we've seen so far.
Jeff Bezos embraced an accessory trend at the 2025 Vanity Fair Oscars after-party, and it worked for him.
The Amazon founder walked the red carpet alongside his now-wife, Lauren Sánchez Bezos. For the occasion, he wore a classic black tuxedo, a white button-up shirt, and dress shoes.
His accessories, though, elevated the look. In addition to a white satin bow tie, Bezos also wore a rounded, diamond-shaped brooch encrusted with numerous diamonds.
Gustav Magnar Witzøe, on the other hand, took things too far at the Met Gala.
The Norwegian billionaire wore a Todd Patrick design for the New York City event. It included wide-legged trousers, a button-up blouse, a satin tie, and an asymmetrical blazer — all of which were white.
He also carried a clear briefcase filled with rose petals, wore a wide-brimmed hat, and sported a semi-sheer overcoat with a long train.
Though the outfit was memorable, it looked more like a costume than a red-carpet look.
Kim Kardashian was one of the best-dressed attendees at the Bezos-Sánchez wedding in June.
Ahead of the wedding ceremony, Kardashian was photographed boarding a water taxi while wearing a skin-tight design from Versace.
The vintage brown dress was sleeveless with a deep, V-shaped neckline and sequin embellishments.
Not only was the 1996 design stunning on Kardashian, but she also accessorized it perfectly with a stack of diamond necklaces and black sunglasses.
At the Met Gala, however, Kardashian was one of the worst-dressed.
Chrome Hearts designed her dark ensemble, which included an alligator-print bustier atop a form-fitting skirt.
The latter had a train that extended down the Metropolitan Museum steps, and her top had off-the-shoulder sleeves. The Skims founder also wore a wide-brimmed hat and layered diamond necklaces.
The outfit's Western vibe didn't make sense for Kardashian, and her accessories were too glamorous to match the edgy ensemble.
Bill Gates had a simple style moment in New York City, and it was underwhelming.
The Microsoft cofounder was in New York City when he was photographed wearing a navy suit.
Though it was tailored sharply, the rest of his outfit lacked depth and detail. He wore suede loafers, striped socks, a blue sweater, and a white undershirt.
A brooch attached to his jacket or a fun watch could have enhanced the look.
LeBron James perfected quiet luxury and coordinated with his wife.
The basketball star and his wife, Savannah James, attended the annual Hammer Museum Gala in May, and both were dressed to impress.
While she wore a semi-sheer ruffled dress from Issey Miyake, LeBron James sported a full Louis Vuitton outfit. He wore black trousers, $1,690 Louis Vuitton sneakers, and the designer brand's $3,800 Damier jacket in tan.
The outfit perfectly complemented his wife's and was subtly luxurious.
Taylor Swift made the right choice when she opted for a simple and sultry Grammys look this year.
Vivienne Westwood designed the superstar's red minidress for the 2025 Grammy Awards. It had a structured bodice, a wrapped skirt, and all-over sparkles.
The outfit proved that red is Swift's color and also nodded to her boyfriend, Travis Kelce. It included a leg chain with a T initial charm, which Swift co-designed with Lorraine Schwartz.
Rihanna has a standout maternity style, but one of her recent looks didn't work.
She was photographed exiting a car in Los Angeles in July while wearing a custom design from Alaïa.
The top half of the outfit was chic and stunning, featuring a tank top with an attached hood. She also wore diamond earrings, black sunglasses, and pink lipstick to enhance the outfit's glamour.
Unfortunately, the musician and business mogul's textured skirt with a 3D waistband distracted from her overall outfit.
Oprah Winfrey experimented with cutouts and looked effortlessly chic.
She wore a burgundy Solace London dress with short sleeves, a white abstract print, and deep waist cutouts for the Bezos wedding.
The dress was a bit daring compared to Winfrey's usual style, but it suited her. She also increased the look's overall elegance with rose-tinted sunglasses and a wavy hairstyle.