Fashion is defined by contradictions that somehow seem obvious, like this one: Really, really rich people do not wear designer clothes.
Okay, sure, there are Birkin customers aplenty and many people who are invited to designer cruise shows and special events around the planet as a thank-you for having spent hundreds of thousands of dollars on clothes and bags. But those are people for whom fashion, or shopping, is a hobby, a habit — like having a boat or an extremely expensive pony.
We’re talking about Western titans of industry here. Tech bros. Media kingpins. People who turn money into more money. They float above the siren call of fashion, preferring that their clothes, either outright boring or slightly slovenly, reflect an unshakable focus on their work.
End of carouselThey don’t have time for a Louis Vuitton Speedy thrown over the shoulder with Rihanna-esque nonchalance. Nor the patience to appreciate the painfully exacting lines of an Hermès calfskin jacket, or the quirky colorways of Chanel’s ballet flats. It’s James Perse T-shirts, pants by Fidelity Denim and Allbirds sneakers for these people, whatever is readily accessible on the most bland floor of Nordstrom. Quilted vests stitched with their company’s logo. A hoodie — Who made it? Who cares? — with whatever pants are comfortable enough that you never have to think about them while working 15-hour days.
But last week at the Sun Valley Conference, investment firm Allen & Co.’s annual summit of tech, finance, and media’s wealthiest and most powerful, something seems to have shifted. Somehow, the billionaires have learned to stop worrying and to love the vicuña. (That’s the mouth-wateringly expensive cashmere that Loro Piana uses for its schmanciest goods.)
There was David Zaslav in what appeared to be a Brunello Cucinelli jacket. Sheryl Sandberg in a Thom Browne cardigan. Wendi Murdoch in a Dior T-shirt. Plus numerous moments of logo-less fashionability: XN founder and CEO Gaurav Kapadia in a white shirt with a funky striped design; Salesforce CEO Marc Benioff in a medallion-studded cowboy hat; and Clear chairman and CEO Caryn Seidman-Becker looking like Gwyneth Paltrow brandishing her quiet-luxury wardrobe at her ski trial last spring.
Even Oprah Winfrey was spotted in head-to-toe Phoebe Philo, the elusive designer who last year launched a namesake brand whose arcane sense of cool is designed to speak to women who have accumulated power through art, music or other aesthetic pursuits. Between meetings, Winfrey was photographed in a pair of Philo’s $1,700 chalk-white jeans with straps at the knee and a $1,700 fluid white turtleneck, looking like, well, anyone else who pairs a white blouse with white trousers, which is to say pulled together but unexceptional. But Winfrey (and the rabid fashion fans who follow Philo’s brand like a cult rule book) was performing a major fashion flex: the quietest assertion that she is playing the game of: If you know — and so very, very few of you know — you know.
“Now I’m finally seeing somewhat of an embrace of, ‘Hey, I do have this kind of cash, and I do want to be comfortable and on-trend,’” said Victoria Hitchcock, a San Francisco-based stylist who works with businesspeople looking to fine-tune their style. Her clients and other leaders in the Fortune 500 universe are gravitating toward Dior, Valentino, Hermès, Marni, Gucci loafers, Yves Saint Laurent, a bit of Chanel and lots of Loro Piana, Brunello Cucinelli and Berluti. “Berluti is it.”
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Facebook founder Mark Zuckerberg was not among this year’s attendees, but he may have started off this zeal for luxury. Earlier this year, the Wall Street Journal reported that Zuckerberg, once notorious for his limited palette of hoodies and T-shirts, is now a devotee of Cucinelli’s T-shirts and is wearing pieces like a fancy little cardigan by Los Angeles sportswear designer John Elliott and a statement-making shearling coat.
Over the past five years, Zuckerberg and Salesforce’s Benioff have worn more and more of Cucinelli’s clothes, suggesting a kind of kinship between the Italian designer’s products and their own — philosophical, emotional, spiritual — that echoes, say, the late Steve Jobs’s taste for black Issey Miyake turtlenecks. It’s a way not only to create iconography, but also to suggest symbiosis between the work of two innovators. Tech types tend to think of their companies with a godlike reverence, even if what they are doing is making day-to-day errands more efficient or a quicker alternative for moving from Point A to Point B. Yes, many people (cynics and admirers alike) see fashion as capitalism run amok. So if designers peddling pricey sweaters can feel good about themselves, shouldn’t people monetizing airport security, too?
But this is not merely a sartorial awakening in the iHeart of eMan. Fashion houses like Cucinelli and Loro Piana, in particular, have spent the past five years courting these customers, including them in high-profile events typically geared toward the media and influencers, such as one-off fashion shows and celebrations.
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In some cases, fashion companies have even hosted events just for tech titans: In 2019, for example, tech execs including Reid Hoffman, Jeff Bezos and Dick Costolo gathered at the behest of Cucinelli in the designer’s hometown for what he called a “Symposium on Soul and Economics.” The group chatted at length about the future of society, with Cucinelli challenging Bezos to think about what impact he would leave 500 years from now, according to GQ.
And in March 2023, Loro Piana opened a store in Silicon Valley that included a special collection accompanied by NFTs. The store also touted a newish program that allows Loro Piana products to be authenticated on the blockchain — an appealing feature for the tech-savvy consumer, sure, but also a way for customers to tout that their nondescript-looking beige pullover sweater is in fact a $5,400 vicuña knit. (Earlier this year, a Bloomberg investigation alleged that Loro Piana does not sufficiently pay the laborers who harvest its vicuña wool.)
The desire to look spiffy seems to have spread beyond these supposedly do-gooder labels, such as Loro Piana and Cucinelli. Sun Valley types are becoming much more well-known than they were five or 10 years ago, vacationing in Lake Como or on yachts alongside A-listers who dress the part. “They are starting to live more of the life of a celebrity. People seem to revere them for their wealth, whether that’s right or wrong,” Hitchcock says. “They want to be included in that world that before they weren’t invited as much into.”
Then again, some Sun Valley participants have always looked spiffy, such as Bloomberg L.P. co-founder and former New York City mayor Mike Bloomberg, who was photographed in Nantucket Reds and a brightly coordinating jacket with the Sun Valley 2024 insignia, or media executive Barry Diller and his wife, fashion designer Diane von Furstenberg, both dressed in eye-catching prints.
Maybe their peers are just catching on. The world’s 0.001 percent have more money than ever, and these people need to find somewhere to spend it. A $5,400 sweater sure makes a dent in that pile of cash.
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