Glenn O’Brien began his career by working for Andy Warhol’s Interview magazine. He’s been the creative director of advertising at Barneys department store, he’s worked as a creative director for Calvin Klein and Island Records and he edited Madonna’s notorious Sex book. In recent years he’s become GQ’s celebrated “Style Guy,” dispensing style and etiquette advice in often drolly hilarious prose.  He talks to CAHIR O’DOHERTY about his new style guide, How To Be a Man.

STYLE. You know it when you see it. Fashion can be bought, but style is something you are born with.
It’s the difference between being a man and being a gentleman. A dude and a dandy.
American men, in the main, don’t give much thought to what they wear most days -- or they often look as though they don’t -- but the Irish man will often give his girlfriend a run for her money in the sartorial stakes. Why is this?

Because dressing up is cultural, O’Brien says. Everyone does it differently.

In his new book How To Be a Man (Rizzoli), O’Brien -- currently GQ magazine’s popular “Style Guy” -- dispenses half a lifetime of rich experience in a column that’s the highlight of each edition.

O’Brien’s new book does for men what E.B. White’s famous book once did for New York City -- it captures the essence of something intangible and gives it back to you straight. How To Be a Man is engaging, brilliant, funny as hell and as uniquely individual as the city in which O’Brien has made his home.

As an essayist, O’Brien has one of the most distinctive voices out there right now, as droll and withering in its way as any meditation by Mark Twain. This book will make you laugh uproariously, it will enlighten you, it has the pleasant effect of increasing your IQ by double digits and it will make you miss your subway stop, I guarantee it.

But what’s O’Brien’s own story? How does a boy from Cleveland come to the big city and forge a megawatt career right off the bat?

Well, call it luck and the 1970s. When pop art superstar Andy Warhol started Interview magazine he had trouble finding staff that weren’t constantly tripping on meth and acid. Enter a clean-cut boy from the Midwest and opportunity knocked.

There was a little more to it than that of course. At Georgetown, his alma mater, O’Brien edited TheGeorgetown Journal (founded by Conde Nast, the person not the company).
In his career he befriended the legendary artist Jean-Michel Basquiat (who brought Madonna to O’Brien’s New York home last Thanksgiving).

Speaking of the Material Girl, O’Brien edited her notorious Sex book. He created the famous Warhol

Factory inspired One campaign for designer Calvin Klein, and while recently sitting at his long, long dining table I can see Basquiat’s Famous Negro Athletes hanging over his sofa.

Debbie Harry, Kate Moss, Lauren Hutton, Tom Ford and Jim Jarmusch sing O’Brien’s praises in the foreword to the book. If New York City has a social center, this must be very near it.

With all this accomplishment, worn lightly, I wonder if he feels close to his Irish ancestry?

“I always felt Irish,” O’Brien tells the Irish Voice. “My father’s side is all Irish, my maternal grandmother was McGinty. I’m McGinty, O’Sullivan. O’Brien in my background. In terms of Irish writers I love Oscar Wilde, but a real big influence on me is J.P. Donleavy. A transplanted Irish American Irish man.”

It was his Irish grandmother who first drew O’Brien’s attention to the cardinal rules of style, and she taught him how important they were when it came to dating girls.

“I was well trained by my grandma, Flora McGinty. She would say, ‘You can’t wear that,’ or ‘You can’t go out looking like that.’

“I remember one night I had a date and she said, ‘You’re going to wear a pink shirt on a date? If I were that girl’s mother I wouldn’t let her go out with you! Put on a white shirt.’ She wanted me to look proper and respectful.”

It was O’Brien’s first lesson that looking good can be a mark of respect as well as a personal concern.

Style is the best possible indicator of substance, after all. In How To Be a Man O’Brien assembles some of the passions of his life -- philosophy, humor, friendship, style and empathy.

“When people ask me to describe it I say it’s a philosophy book disguised as a humor book disguised as an advice book,” he says.

Why, O’Brien reasonably asks, should the female surpass the male when it comes to dressing up? Most American men may look and dress like the mannequins in the Gap, but the Irish and the Europeans often take more interest in their appearance.

A lot depends on where you’re born. In fact in some African tribes like the Wodaabe, O’Brien writes, the men are spectacularly flamboyant, the real beauties.

“I think fashion can be repressive but style is sort of the opposite,” says O’Brien. “When I was reading this book for the first time I was very taken by the idea of style as a political force, you know what I mean?

“I’ve been accused of being really political in this book, which is funny because I think most people probably think it’s just a guide that tells you how to tie a tie.”

Men developing a personal style, a personality, is something that goes against conformity, against being regimented. American men are trained to be shy and to stay in their place, and so if you can get people on the road to being non-conformist it opens up a lot of possibility.

Style, says O’Brien, is what you can’t forget. It’s as individual as a fingerprint or your DNA, but it’s usually much more entertaining.

It is, he writes marvelously, our visual and behavioral signature. And if all that’s true -- and it is -- then isn’t a good idea to ensure your signature is legible?

“I just observed that a lot of men look stupid, which I think is something that happened in my lifetime. Men used to have more of an idea of how to look because they were trained as children to have certain standards or respect certain occasions,” O’Brien maintains.

“I think that parenting broke down under the influence of TV or something. Boys were just put into uncomfortable clothes. They were dragged around in football clothes and sneakers. So they get to college and they don’t know what to do. Then they get a job and they really don’t know what to do.”

It’s non-conformity, not narcissism, that’s at the root of style. Most people are other people, wrote

Oscar Wilde once. Nothing is so rare in a man as an act of his own. A real man will stand up and let his freak flag fly, he won’t be afraid to be himself, anywhere, ever. In fact he’ll revel in it.

That’s what makes O’Brien the Style Guy he’s celebrated as. But how did the famous GQ column get started?

“I was a contributing editor for Details and editor Joe Dolce had an idea for a style advice column called

Your Gay Friend. It was years before the Queer Eye for Straight Guy show. They were looking for someone to write it and one of the board said, ‘I think Glenn should.  Everybody laughed.” (O’Brien is married, with a 10-year-old son).

But it was obvious he was the ideal candidate. So Your Gay Friend turned into the Style Guy and a fashion icon was born.

Being heterosexual and surrounded with fashion industry gays, O’Brien can easily interpret between all of their identities like any New Yorker.

“You can’t tell who’s gay and who’s straight anymore except for sex. In other areas it seems that straight guys know more about how to behave. I guess our culture is catching up,” he says.

“We’re learning how to cook and how to eat. It used to be considered un-masculine to cook.”

But O’Brien is used to finding himself ahead of the herd. Everything he has done in his career he has done under the guise of doing something else.

“I had a music column in Interview for 12 years but really I wrote about everything. I always wanted to be an essayist, but I understood it was going to be a hard road to hoe. I didn’t see openings for essayists in the Help Wanted ads,” he says.

“Being an essayist was a bit like being an aspiring stonecutter, shepherd or flutist. Not a growth industry. And now, when we need it more than ever.”