Taylor Lorenz’s Power User
Taylor Lorenz’s Power User

Why Palantir Is Selling Tennis Skirts (w/ Lawrence Schlossman)

September 10, 2026

AI Summary

5 min read

Why Palantir Is Selling Tennis Skirts

In 1983, a group of exhausted Apple engineers received gray hoodies emblazoned with a misspelled "Macintosh" on the front and the slogan "90 hours a week and loving it" on the back. The finance team had commissioned them as an inside joke about the grueling work schedule. Forty years later, Palantir is selling chore coats, tennis skirts, and boxing gloves. Lawrence Schlossman, co-host of the menswear and culture podcast Throwing Fits, joins Taylor Lorenz to trace how tech company merch evolved from employee inside jokes to startup status symbols to a wearable expression of ideology—and why the current AI boom has produced a strange paradox: companies obsessed with the future are dressing themselves in trends that peaked a decade ago.

From Apple's Preppy Catalog to the Dot-Com T-Shirt Graveyard

Apple's 1986 "Apple Collection" catalog was the first serious attempt to turn a tech company into a lifestyle brand. It featured professional models in preppy sportswear—pop collars, technical fabrics, primary colors, and understated logos that looked more like Ralph Lauren than a computer company. The collection flopped. "Tech at that time, yes, the Mac computers were making tech more accessible, but you were still seen as a geek," Lorenz notes. The average Apple fan in 1986 did not look like the Chads and Staceys modeling the gear.

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What you'll learn

  • 1 (03:13) **Lawrence Schlossman on the Evolution of Tech Merch** - The Throwing Fits co-host joins Taylor to trace how tech company apparel went from employee uniforms to startup status symbols to a wearable expression of ideology.
  • 2 (03:53) **The First Piece of Tech Merch: Apple's "Macintosh" Hoodie (1983)** - Lawrence describes the iconic internal sweatshirt made for Apple engineers working 90-hour weeks, misspelled with a "K" as an inside joke.
  • 3 (05:49) **Apple's Abandoned Lifestyle Brand: The Apple Collection Catalog** - Apple attempted to launch a full fashion catalog in the 80s, selling preppy sportswear and accessories far ahead of its time.
  • 4 (10:29) **The Dot-Com T-Shirt Era: Promotional Swag as Relic** - The 90s and early 2000s saw tech merch devolve into cheap, logo-heavy t-shirts given away at trade shows, now collectible as novelty items.
  • 5 (14:33) **Google's Early Merch: Proto-Funko Pops and Developer Swag** - Google's Android figurines and t-shirts for Maps power users marked a shift toward collectible desk toys and community badges.
  • 6 (18:12) **The Octocat Era: GitHub's Millennial Optimism Mascot** - GitHub's half-cat, half-octopus mascot became an iconic desk figurine in the 2010s, embodying the tech industry's playful, optimistic self-image.
  • 7 (19:31) **The Patagonia Vest: Tech's Unofficial Uniform and the Tech Lash** - In the 2010s, tech workers adopted Patagonia vests as a status symbol, leading to a backlash when Patagonia banned finance and tech companies from customizing them.

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Guests on this episode

Taylor Lorenz

Show Notes

Why are people buying OpenAI sweatshirts, Claude “Thinking” hats and Palantir chore coats?

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I sat down with Throwing Fits co-host Lawrence Schlossman to unpack the rise and fall of tech company merch. From Apple’s bizarre 1980s catalog lifestyle flop to dot-com bubble eBay relics, the rise and fall of the infamous corporate Patagonia fleece vest, and today’s ultra-hyped drops from companies like OpenAI, Anthropic, and Palantir, we discuss why the most powerful AI companies on earth are suddenly trying to buy their way into high fashion, menswear, and cultural relevance.

We also talk about OpenAI, Anthropic, Palantir, Apple, Meta, Patagonia, Cash App, tech bro fashion, menswear culture and the influencers making AI merchandise aspirational.

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