The A.I. Founder Starter Pack: How to Make a Uniform Look Like a Strategy

When several hundred of the most powerful people alive gathered in Idaho this month for the Allen & Company conference—the invitation-only retreat the press calls summer camp for billionaires, held July 7 through 11—the tech founders who now outnumber the media moguls arrived dressed to a man in the same costume, with nary a suit in sight. The uniform is a plain gray T-shirt that looks like it costs $12, but in fact costs $300, and that gap—between what an outfit looks like and what it rings up—is the entire organizing principle of how the technology class dresses now.

The template belongs, as all of it does, to Steve Jobs, who asked Issey Miyake to make him a lifetime supply of black mock-necks and paired them with Levi’s and New Balance until the whole thing passed for monkish indifference. It was nothing of the sort. “He made me like a hundred of them,” Jobs told his biographer, delighted. The costume of not caring was, even then, custom-ordered and signed by a designer, the opposite of thoughtless dressed up as thoughtless. Every founder since has been answering that same black turtleneck, and the answers have lately sorted into houses of worship.

There is the Zuckerberg school, which spent a decade in the gray Brunello Cucinelli tee—north of $300 a shirt, because the man who could buy Hanes by the container chose Italian cashmere-blend instead—before undergoing the most scrutinized “glow-up” in Silicon Valley. The Zuckerberg of today wears gold chains, shearling, oversized graphic tees and, in the video that ended Meta’s fact-checking program, a Greubel Forsey watch that retails for $895,500 and takes roughly 6,000 hours to build by hand. Asked to explain the sudden horological awakening, he offered the finest sentence in modern menswear: “Watches are cool.” There is the Jensen Huang school—he skipped Idaho this year—which is a single garment worn for two decades, rooted in the black moto jacket he has made his own, most memorably a Tom Ford number from the GTC 2024 keynote that cost nearly $9,000, embossed to look like lizard because California bans the real thing for ethical reasons.

And then there is the Sam Altman school, the purest form of the creed, expensive-looking-cheap casual, undone by a single conspicuous object. Altman turned up to last year’s Sun Valley in a plain tee and Vuarnet sunglasses, having said, with a straight face and a jab at the man in the shearling, “I don’t like smart glasses.” He was back again this month, meeting the cameras head-on beside his board chairman as though he had nothing to hide. Herewith, the 2026 A.I. founder starter pack—18 pieces for the man who wants to look like he’s too busy solving intelligence to have gotten dressed, and who understands that this is the most expensive look there is.