Perennials: Michael Hainey

To celebrate this year’s Perennials collection, we travelled from New York to London to Paris, spending a few days with friends whose style we admire to find out how they wear Drake’s, and to see how these clothes have become trusted companions in their everyday lives. 

Michael Hainey is a writer and editor whose career spans decades, a presence in American journalism marked by curiosity and insight and a love of storytelling. At GQ and Esquire, and more recently at Air Mail, he has built a reputation for thoughtful, wide-ranging profiles — sitting down with Hollywood movie stars and musical icons — and intimate explorations of place and culture, from his local bar, The Corner Bistro, to the Rothko Chapel. He is also the author of the New York Times best-selling memoirAfter Visiting Friends, which he is currently turning into a film. 

He recently guest edited an issue of our in house magazine, Common Thread, and we’re very pleased to have him star in our Perennials campaign, and spend a day with him at his home in Greenwich Village. 

Hello Michael, what was the creative highlight of 2025 for you?  

The conversations I’ve had with directors about the screenplay I co-wrote — which is an adaptation of my book — with my partner Steve Kloves.  

What about personal?

Running my first marathon. After a long time away from the sport, I returned to it this past year and then set a crazy goal for myself: running the New York City Marathon. The entire experience was peak-life. 

You’ve been working in the magazine and publishing business for 35 years — what’s the most valuable lesson you’ve learned?  

As a writer, reporting is your best friend. Not just in journalism, but in fiction and essays as well.  

And what keeps you excited and inspired to keep on writing?  

The ability to create your own worlds.  

What do you still enjoy about New York?  

That everyone is from somewhere else. That the optimism never quits. That it's forever regenerating itself in ways you love or that drive you mad. That you can discover beauty and inspiration in the smallest moments and least-expected places, like the hawk that often sits atop a church spire outside my window. That in its soul it’s a giant small-town.   

What gets you feeling nostalgic?

Anything digital inevitably makes me pause and think what a gift it was, at least in regards to building a creative mind, to come of age in a world that was largely analog and certainly less hyper. 

You’ve interviewed just about everyone in your years as a writer for magazines, who was the most surprising, and also the least?

Most surprising would be a tie between Clint Eastwood and Keith Richards. Who they were one-on-one with me — vulnerable, kind, gentlemanly, modest, ruminative, wise, soulful — was vastly different from their public personas. 

Least surprising, and I mean this as a compliment as I was relieved to see the man I sat knee-to-knee with in his dressing room was the same man I had always believed, and hoped, he was ever since I discovered my brother’s LP ofDarkness on the Edge of Town when I was 14 — Bruce Springsteen. Deeply reflective, generous, sensitive, kind, wise, humble. 

What’s a rule you’ve always ignored?  

Don't play with matches. 

You’re a very stylish man, what do you enjoy most about getting dressed in the morning?  

When my wife tells me I look good.