The former Esquire chief Jay Fielden, a proud son of Texas, commands the space between the men’s style industry and modern-day magazine journalism.
Meet Jay’s Australian Shepherd, Badger, perched here in the ’93 Land Rover Defender. Outfit: The jacket is from Denis Frison, a tailor who likes to work with deadstock fabrics. This bold herringbone tweed is from the seventies. The tartan button-down is from Ralph Lauren. The Charvet knitted tie is one of a large collection but stands out, as it was a gift from Lee Radziwill. The cord trousers are P Johnson, one half of a full corduroy suit. The boots are Russell Moccasin, made in Wisconsin – Hemingway wore them, and Jay calls them the greatest boots ever made. The shooting socks are Pantherella and the pocket-square is Charvet.

Jay Fielden, I have decided, is what happens when Jim Morrison and F. Scott Fitzgerald reproduce. My first close encounter with Fielden, the former Editor-in-Chief of U.S. Esquire, Men’s Vogue and Town & Country, came during his Esquire tenure, in Brunello Cucinelli’s homeland of Solomeo, Italy. It was an extravaganza that attracted international media of all types, and muttered in reverent tongues among journalism’s finest was the gossip that Jay was on site. His reputation proceeded him, and we all hoped for a chance meeting. He came across exactly as we wanted him to: a rock star with an intellectual aura.

Jay’s successful career in the industry was predestined from his days growing up in San Antonio, Texas, where there was a Ralph Lauren Polo store in which he got a job while still at high school. He gravitated towards men’s magazines in book shops and learnt the language of style of the late eighties, which owed its allegiance to an older, professional demographic. Moving to Boston for college, he took with him his crunchy Texan accent and an apparent knack for selling Ralph Lauren, as he picked up a job at a store there, too. But magazines were his calling. “I wanted to find people who can reconcile great writing and style,” he says.

He is now based in Connecticut, and at a juncture in his career where he can not only look back at an ambition fulfilled but forwards, in his pro-consul years, as he keeps fighting the good fight. He kindly allowed The Rake to visit him, where we were witness to the fact that with Fielden, his style, or rakishness, is not just a job, it’s an identity.


August 2021


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