You should think—really think, like, deeply—about what you wear. That’s the impression Avery Trufelman, and her podcast Articles of Interest, will make on you. That refers not to how it fits or whether to tuck in your shirt but to the meaning behind your clothes. The stories they tell the world. The historical, anthropological, and philosophical implications of a garment. You know, deep stuff.

“There are so few places where we really get to think about fashion as this strange exercise in groupthink, this strange lens to look at history,” she says about her podcast. “Something beyond what to buy, where to shop, or what celebrities are wearing.”

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Emily Soto

The best example of Trufelman’s view of fashion is the third season of Articles of Interest, “American Ivy.” It’s a serialized season (as opposed to others with stand-alone episodes), in which Trufelman charts the history of Ivy League style. I won’t spoil it, but she provides one of the best style histories I’ve ever consumed. She’s able to use the podcast format—which means you can’t actually see the clothes she refers to—in an incredibly compelling way. It’s her voice, her lucid descriptions, and her ability to tell a story that keep you on the edge of your seat during a podcast that’s ostensibly about navy blazers and chinos.

To give you a sense of the real-world impact of “American Ivy,” look at Take Ivy, a 1965 Japanese photography book chronicling style on America’s most prestigious campuses. Before “American Ivy,” the book was exceptionally rare in America. Only the most hardened style enthusiasts owned copies, which were hard to come by and priced accordingly. Now? It’s very likely a copy of Take Ivy is sitting in the fashion section of your local bookstore for retail price. It’s certainly on Amazon. Trufelman calls it “one hell of a coincidence,” but Esquire can call it like it is: The book is relevant to a mainstream audience because of that season.

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This reflects a more widespread trend of fashion becoming a popular intellectual pursuit on the Internet. Of course, academics have long discussed these topics, designers have always considered this stuff, and certain corners of the Internet have delved into the thinking for years. After all, we’re a decade and a half past the #menswear blog era. But Trufelman is part of a new, more expressly intellectual wave that’s finding that there is widespread appetite for deep-dive fashion histories and criticisms on the Internet.

We each list off some names. I mention Derek Guy, an Esquire contributor and the creator of his own blog, “Die, Workwear!” Known as the Menswear Guy on X—where he has more than 1.3 million followers—Guy has reached an audience far beyond the fashion community and appeared in two Articles of Interest episodes. Trufelman mentions Bliss Foster, who’s been doing fashion-theory deep dives on YouTube for years. Recently, Foster joined her on a reporting trip to Georgia. I call out Nymphet Alumni, another one of these fashion and culture podcasts, where Trufelman has been a guest. In other words, there are a lot of people thinking very deeply about clothes these days.

Trufelman believes, and I agree, that everyone should adopt this sort of conceptual thinking. “That’s the biggest joy—falling deep, deep, deep into a world,” she says.

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Emily Soto

Lead image: Shirt by Marina Moscone; vest by Maryam Nassir Zadeh; pants by Vivienne Westwood; ring by Dunton Ellerkamp; vintage loafers. Above: Vintage blazer; shirt by Usonia; skirt by Art to Ware; ring by Old Jewelry; boots by Trippen.

That doesn’t mean you have to read designer notes from runway shows or pursue color theory. Conceptual thinking about fashion can be pure history—the why of a garment or the how and where it was made. Trufelman says this is something menswear enthusiasts already have a great grasp of, and she’s found it easy to tap into in her line of work.

“I love the bros,” she says. “With menswear, you only need to say, ‘I see you’re wearing selvedge denim.’ ” Then they tell her an entire history about the factory that makes their pants. “I think mansplaining is a benefit,” she adds.

Well … maybe. But that idea of thinking critically about the history and application of fashion is undeniably true. If you listen to other episodes of Articles of Interest, you’ll hear Trufelman talk about religious mandated modesty, prison uniforms, even nudity. In every episode, you get a different look at the ways in which fashion is a language. Fashion can be used to devalue or dehumanize, but it can also be a thing of great significance, a sign of love. Dressing up for a friend’s birthday shows them how much they mean to you. Your outfit is semiotics, projected out to the rest of the world. So before you get dressed, consider Trufelman—and then think about what you’re really trying to say.

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