Yesterday, we lost a real one. Glenn O’Brien, one of the last true purveyors of “cool” in our increasingly bland and uncool world passed away due to complications from pneumonia.

Over the course of his career, O’Brien wore many hats and each of them fit well. To review his wide-ranging resume is to marvel in awe of a man who did everything you wish you could have before you were even born. If it was cool, O’Brien was there.

A cohort of Andy Warhol and the first editor of Interview, O’Brien didn’t just have his finger on the pulse—he was the pulse. He was a sharp editor who basically invented the title “editor-at-large” because he hated the constraints of the office. He held down tenures at High Times, Allure, Details, and Spin, among others, and developed a taste level so trusted that Barneys hired him as creative director of its in-house ad agency in the mid-’80s. He also created the cult classic public access show TV Party, which featured likes of Jean-Michel Basquiat, David Bowie, David Byrne, Iggy Pop, and Robert Mapplethorpe—just to name a few—before they blew up.

O’Brien will be remembered for many things, but many, like myself, will hold dearest his 15-year stint as Details and later GQ’s original Style Guy. Even as a 12- or 13-year-old without a single dollar to my name, I’d pick up an issue of GQ and read his section just to be told how to dress. In one moment, he could describe the details of the perfect dress shirt and in the next, advise a man on how to navigate a troubling time in their life, all in a way that felt like he was right there with them.

Glenn O'Brien
Image via Getty/Patrick McMullan

That was the beauty of O’Brien’s guidance. His advice was never really about buying the clothes to dress better. It was deeper. It wasn’t about keeping up with the trends, it was about staying true to yourself. For budding men like myself, his lessons felt more fatherly than they did stylistic and left a mark on me and many others more than any explanation about the perfect suit ever could. O’Brien literally wrote the book on cool, only to revise it and made it better later. His honesty was brutal and cutting at times. But his openness about what and who he liked meant something when others were more likely to play nice to save face.

I, unfortunately, never had the pleasure of meeting O’Brien in person and I will always wish I had. But he played an important role not just in how I learned to dress, but how I learned to live—and there was no better person to take lessons from.

Until his final days, O’Brien was pretty much unstoppable, whether he was showing off his incredible New York City apartment filled with art and memorabilia most of us had only heard of, openly airing grievances over his departure from GQ, or being the don’t-give-a-fuck voice that we all wish we could be.

To put it simply, O’Brien never missed a step. Without him, we would have missed many. But most of all, we will miss him.

Rest in peace.