“Style never goes out of fashion; fashion goes out of style.” — Mickey Drexler
Last week I was in New York where mother nature reminded us that winter is coming. Meetings with potential investors for Sugar Capital at the Equal Emerging Manager Summit. Everyone commenting on our momentum. On Grüns. Coffee with Alex Stone, founder of Split, our portfolio company building content-to-commerce technology. I visited Jessie and Brian, the married founders of Loeffler Randall. Philippe and Justin, the founders of Refinery29, our archnemesis back in the POPSUGAR days. Now we’re investors in their new company. Funny how competition turns into partnership. Hillstone for dinner (shoutout to Bethesda losing theirs), funny how some things taste even better after thirty years. That kind of week.
But the real highlight was Mickey Drexler at the Alex Mill corporate offices in Manhattan. He’s 81 years old and runs the brand with his son Alex. Every industry has its Jordan, its Tiger, its Ohtani. Retail has Mickey. He built Gap from $400 million to $14 billion. Launched Old Navy and hit $1 billion in four years. Turned J.Crew into a cult brand. Sat on Apple’s board helping Steve Jobs invent the retail store as theater. Unlike most GOATs who retire, Mickey is still on the floor at 81, still running plays, still obsessing over product. Not growth metrics. Not customer acquisition costs. Product.
Standing in those offices, I told Mickey I wanted The Peacoat. He immediately took me over to where his merchants and designers were meeting and told them they should make The Peacoat. Then he began teaching all of us about “The.” The Oxford. The Tote. The Peacoat. How great brands become known for key definitive products. It’s never “a peacoat.” It’s The Peacoat. The one. The definitive version.
Apple does the opposite. iPhone. Mac. iPad. No “the.” They treat products as proper nouns. It’s Steve Jobs’ philosophy: fewer words, more power. But Mickey’s retail instinct goes the other way. In fashion, “The” signals curation and authority. We did the same thing at Everlane with The Weekender. Mickey doesn’t use a computer. Never has. He walks the floor, touches the fabric, trusts his eye. It’s a rare quality, and it’s about to become the most valuable skill in retail.
On the flight home I read notes from my partner Will’s conversation with Violet, our portfolio company building infrastructure that connects brands to AI shopping platforms. Every brand will need this.
Here’s why. For 30 years, retail distribution has been a rigged game. You paid for shelf space, bought Google AdWords, or paid Amazon for sponsored placement. Mediocre products with big marketing budgets could outspend great products with no budget. Distribution always trumped quality.
Agentic commerce breaks that model. When ChatGPT recommends products, it doesn’t care about your ad spend. It reads every review. Every Reddit thread. Every Wirecutter teardown. A shopper asks, “I need a durable white t-shirt that won’t shrink.” The AI shows the one that 50,000 people said held up after 100 washes. Finally, after three decades of pay-to-play distribution, the best product wins.
This is why Mickey Drexler matters more in 2025 than in 2005. Agentic commerce rewards exactly what he’s always preached: quality, curation, timeless design, emotional connection. When an AI agent scans the internet for “best men’s oxford shirt,” Alex Mill surfaces. Not because they bought ads, but because people genuinely love the product. The same goes for Marine Layer’s impossibly soft fabrics. Or Everlane’s transparent pricing. Or Loeffler Randall’s shoes that women actually keep and wear for years. AI doesn’t lie. It aggregates truth.
I watched this happen in media when we built POPSUGAR. In the early 2000s, traffic was bought. Then social algorithms started favoring engagement, and suddenly quality mattered again. Agentic commerce is the same shift, but for products. YouTube destroyed the networks’ monopoly on who gets airtime. When gatekeepers fall, merit rises. That’s what’s happening now. The gatekeepers were Google and Amazon and Facebook, deciding what you saw based on who paid the most. Now the gatekeeper is an AI that reads everything and recommends the best. That’s not a feature update. That’s a transfer of power.
The next decade will belong to merchants like Mickey. To founders who care more about the drape of a shirt than CAC/LTV. To brands that build for longevity, not virality. When an AI agent is your customer’s proxy, you can’t fake quality. Mickey taught me that great merchants become known for definitive products. The Peacoat. The Weekender. The one customers trust. In agentic commerce, that philosophy finally has the distribution it deserves. He spent his life teaching people to trust their eye. Now AI is teaching the market to do the same. The moat isn’t marketing anymore. It’s product.
Amazon doesn’t understand this yet. They’re blocking AI crawlers and building Rufus, their ad-laden chatbot, because they can’t imagine a world where the interface isn’t theirs. But Walmart does. Marine Layer does. The great merchants do. They know that when the interface changes, the winners are the ones who were already focused on making something worth recommending.
I’ve seen this pattern destroy incumbents as both founder and investor. Newspapers ignored Google until classifieds evaporated. Sears ignored eCommerce until the catalog became a museum. Blockbuster ignored Netflix until stores became Halloween pop-ups. The pattern is always the same. The interface shifts. The incumbents protect the old model. The winners are already building for the new one.
The next shift is here. The interface is conversational AI. And the brands that survive will be the ones that were always building for quality. Because now there’s nowhere left to hide. No ad budget to paper over a mediocre product. No SEO tricks to game the algorithm. Just your product and 50,000 honest reviews and an AI that reads every single one.
Thirty years of marketing bullshit just met an algorithm that reads reviews.
P.S. Yes, I wrote an essay about not name-dropping. Then I wrote that opening paragraph. The irony isn’t lost on me.
Loved catching up with you. And grateful you see a trend of quality finally getting more credit than ad spend.