An Interview with Esquire Editor-in-Chief Michael Sebastian

Discussing his career, style, adversity, the manosphere, leadership, fatherhood and much more.

Prior to this interview, I had only talked to Esquire’s Editor-in-Chief, Michael Sebastian, a handful of times, mostly on the street outside of fashion shows or briefly at events. Our first proper conversation was at Esquire’s offices. He invited me to meet and chat, and he gave me a tour, complete with a look at the archive room which is uniquely fascinating since Esquire was founded in 1933. He pulled out an issue from my birth year and month—February, 1992—a really fun time capsule and a charming end to our afternoon together.

For someone in such an esteemed position, he hasn’t been interviewed much. If I could, I would have featured him by now for Five Fits, so I was thrilled when he replied to my text to interview him for my Substack enthusiastically. Below is a conversation we had in Michael’s office, spanning many substantial topics. It’s a great view into the mind of an industry veteran who takes his post seriously—but not tediously so.

What has your work history been like? How does one become the editor-in-chief of Esquire?

Good question. I started working in newspapers in Chicago where I’m from—local newspapers at first covering school board meetings and police blotters and all that stuff. I did that for a couple of years. I worked for a music critic at the Chicago Sun Times for a little while, then worked for a business trade publisher, and then moved to New York. I worked at Ad Age as a media writer and columnist. Then I came to Hearst as the news director of the magazine's digital division, which is a title that doesn't exist anymore but did ten years ago. I then became digital director of Esquire and did that for a few years before becoming editor-in-chief.

I had a clear vision for what I knew this brand could be. It’s one of the most iconic media brands in America. It's 92 years old. Ernest Hemingway wrote for the first 20 issues of the magazine. James Baldwin wrote for it, F. Scott Fitzgerald, you name them. We've done all kinds of seminal things, but at the time, it felt like we were resting on our laurels and that the world was beginning to move past Esquire, which has always been a brand that has sought to meet the moment. The idea was—for lack of a better term—to bring it into the 21st century. Not only with the kinds of stories that we did, but where we did those stories, too. You're a part of that, you know? Doing very cool, inventive street style around interesting people [for the site]. Something that we didn't do before but we do now.

What’s a typical day in the life of Esquire’s editor-in-chief?