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It was in the shallow end of the pool at the American Express Fine Hotels & Resorts property Rosewood Sand Hill (rooms from $595) that I began to understand the current state of Silicon Valley. The sprawling, ranch-style property is about 45 minutes south of San Francisco, on what locals call “the Peninsula.” The Peninsula can include Palo Alto, Atherton, Woodside, Menlo Park, or Silicon Valley. “But no one around here ever says ‘Silicon Valley,’ ” the concierge corrected me politely, as she drove our golf cart past a phalanx of Matrix-looking security guards. Ahead, my cedar suite was framed by the Santa Cruz mountains and sheared Italian cypress trees launching out of the ground like ballistic missiles.
Palo Alto was founded in the late 1800s, and quickly attracted wealthy San Franciscans like Leland Stanford, who brought his racehorses here and, in 1891, founded Leland Stanford Junior University. Horses are still around. Needless to say, Stanford University is too. The area is surprisingly beautiful for one that’s known to the rest of the world for what happens inside its office parks.
The Rosewood is tucked off Sand Hill Road. What Madison Avenue is to advertising, Sand Hill is to venture capital. The legendary dealmaking and carousing and caviar-dolloping at the hotel’s bar are at odds with the meditative landscaping. Rosewood’s tiered property yawns softly from behind ragged hedges, stretching between the National Accelerator Laboratory—a two-mile stretch of facilities advancing particle physics and X-rays—and two golf courses. During the week, the Rosewood is the “work-from- hotel” scene for visiting VCs, East Coast-based Googlers, and an international set of Very Important Guests, in town to network/broker/disrupt/pitch.
But I’d been told that a dramatic shifting of the tides had begun to take place on weekends, when young, moneyed members of Rosewood’s Lifestyle Membership program descend. They are the new locals, who have moved here from San Francisco and beyond and have found an ad hoc country club. Come Saturday morning at the valet stand, gone are the idling, blacked-out Denalis. Instead, there are recharging Fiskers and Teslas, Range Rovers and Maserati SUVs in metallic sheens. And, at the pool, “there’s an actual scene,” as one young woman put it, whispering into her phone at the pool bar–slash–botanical garden.
“It’s the new Palo Alto versus the old Palo Alto right now,” Rafael Ortiz told me later. He’s somewhere in the middle. A veteran of Apple, Ortiz recently launched Project YX, an app-based wardrobe- curation service. Like a lot of people, he’s struck by the changes on the Peninsula. “And it’s just the beginning, he says.” He mentioned the Pace Gallery’s opening in Palo Alto. I told him that the area is said to sell more cashmere and Teslas than any place on earth. “I wouldn’t be surprised,” he said.
Ortiz explained that with the incredible amount of new wealth in the area—the Peninsula now has more tech billionaires than any place on earth, and the number will only grow with more IPOs on the way—both social and shopping mores are evolving. “In Palo Alto, money is still extremely hidden. People spend big on things seen as acceptable—cars, homes. You can get away with flying private because your jet isn’t parked in your driveway.” The residents of Palo Alto, he says, are not your typical luxury customers. “They don’t trust conventional sales people.” Besides, he said, some of them want to change the whole thing. “The personal luxury-goods business is a $300 billion-a-year industry. This area is interested in attacking or disrupting anything that is a big industry.”
At the open-air Stanford Shopping Center, I met Cristóbal Ibarra at Jeffrey. The 27-year-old sales associate grew up in East Palo Alto and, from the sales floor of stores like Fendi, has watched the area evolve. “Ten years ago, the Peninsula was polite. The old-money and Wil- kes Bashford–type stores.” He called out more of the town’s recent additions: the contemporary-art-filled restaurant Selby’s; the shopping nights Jeffrey will soon host at the Rosewood; Hermès, which opened a 6,000-square-foot store a year ago. “Go look at the line there,” he said. “You have to see it. And it’s not tourists.”
I had no trouble finding the luxury end of the mall. I just followed the crowds to the bold-faced brands (Cartier, Neiman Marcus) looped around a black- marble infinity fountain. At Hermès I watched a fortysomething man buy three pairs of $700 sandals with H-shaped uppers. “I’m going to the Hamptons,” he said with a shrug.
“That’s so Palo Alto,” Mary Gonsalves Kinney, a personal shopper who works with many tech C-suiters told me later. “The new Palo Alto anyway. When they travel, they get to wear all the clothes they are dying to pull out.” The former celebrity stylist explained that her clients are men who are retired at 32 and on their second start-up. Or women who are trying to get to CEO in what is still a male-dominated—and very anonymously casual—business environment, one in which appearing to care about your image means you aren’t taken seriously. “Their wardrobe can’t interfere with their value.”
Of course, her clients are faking it: Choosing Thom Browne button-downs or unmarked knits from Brunello Cucinelli, they appear to blend in with their employees. No capital F fashion. Of course, that might change, as the Peninsula continues to coalesce into a single community.
Back at the Rosewood, I swam to the north end of the pool, submerged in a half-million gallons of water poured into a French cross surrounded by a grove of olive trees. Above me, a server dropped off a tray of yellowtail ceviche, wood-fired pizza, and Sonoma Chardonnays to a foursome on chaise longues. Umbrellas the color of turmeric rendered a sepia-toned selfie. The conversation bounced from a recent product launch in town and the new rooms at the Nobu Hotel to Atherton property values and the sale at Nordstrom to the yellow-corn velouté at the Village Pub in Woodside near all the horse farms.
“Do you miss living in San Francisco?” one of the men asked the couple opposite him. His corrugated torso rose from Orlebar Brown trunks. The hair on his head, cheeks, and chest was clipped to precisely the same length.
“No!” the other couple said at the same time with a laugh.