History’s Finest: The Legacy Of Glenn O’Brien

I was in a niche boutique menswear store on a moist summer’s day in New York. I was picking out potential shirts for my sister’s wedding, which had a strict insistence on casual attire. But we all know ‘wedding casual’ doesn’t mean the same thing as ‘casual’. I needed help. So it wasn’t a shirt that caught my eye, but a book. Blending in like just another piece of furniture sat How To Be A Man by Glenn O’Brien. As I have been manoeuvring my way through the mysteries of manhood over the past decade or so, this subject is an inherent interest of mine.

Glenn O’Brien and Andy Warhol.

As one of New York’s most famous fashion connoisseurs, I expected Glenn’s book to be filled with suiting suggestions, hairstyles, and maybe a couple of cocktail suggestions. My assumptions were correct – to a degree. What I found was advice on subjects from grooming body hair, to courting women, to finding the perfect-sized lapels. But most importantly, Glenn’s work taught me why these things matter, and why culture is important and must be maintained in this era of ‘casual Friday’s’ and poor manners. This is the life and times of one the world’s finest dandies.


‘Never assume that beautiful people are not equally outstanding in the brains department.’

Glenn O’Brien was born into the frosty streets of Cleveland, Ohio in 1947. The post-war America that Glenn was born into was rife for cultural change and he saw an opportunity to be part of that shift. Glenn started off his writing career well, editing the Georgetown Journal during his time at Georgetown University. This Journal was founded by the legendary Conde Nast and would be the first of many times Glenn would follow in the publisher’s footsteps.

Glenn O’Brien quickly became intertwined with a budding New York youth culture and became fast friends with artist Andy Warhol. Glenn was a cultural connoisseur and soon gained multiple forms of employment as a writer, editor, and contributor. He was New York’s go-to man on how to act, how to dress, and how to live. This wouldn’t change for his whole life.


‘Always be on the lookout for people who remind you of you.’

Glenn’s first notable work came as editor of the Interview in 1971, a position he would maintain for three years, but continue to contribute to for 20 years. As well as fashion, Glenn grew through the ranks of punk-rock reviewers, mixing his taste for the proper with a need for anarchy. During his peak cool-ness, Glenn hosted a public-access TV show called TV Party which featured prominent figures of the time such as Jean-Michel Basquiat and music acts like Blondie.

Being a pop-culture connoisseur wasn’t Glenn O’Brien’s only trade. The fashion icon also edited books for Cathy Acker, Terence Sellers, and even Madonna. As his fame and credibility began to soar, he also began to contribute to cultural cornerstones like Allure, Harper’s Bazaar, and ArtForum Magazine.

RELATED: ‘The Curious History of the Suit’


‘We must have the courage to go back to the age-old tradition of ritual and dress code. We must have the courage to turn the shoddy away at the door.’

In 2017, Glenn O’Brien passed away at 70 years old. Guest Of A Guest named him the ‘last cool guy of New York’, and Madonna remembered him as ‘an amazing soul and a creative genius.’ Thankfully, Glenn is survived by his sizeable back catalogue of essays and articles. His influence stretches far beyond the streets of Manhattan and Brooklyn.

Glenn OO’Brienwas one of the last bastions of proper culture in the West. He argued in favour of leaving thank you notes after a night at a friend’s place, always overdressing (never underdressing), and keeping cool alive. He was named one of GQ’s most stylish men and will forever be immortalised as ‘The Style Guy’ – a title the commands respect and admiration from all the cultural corners of NYC and the rest of the world.


Jay is a writer and content producer for The Versatile Gent.

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