Photo: Astrid Stawiarz, Getty Images

Glenn O'Brien is one of the multihyphenated style icons who has embodied the downtown New York scene for decades. A member of Andy Warhol's Factory and formerly the editorial director of multiple magazines, O'Brien now writes GQ's Style Guy column, doling out sartorial advice to less fashionable men. He recently wrote "How to Be a Man," a book of essays that aims to teach men today how to be gentlemen. StyleList caught up with O'Brien and talked style, fashion, arts and music.

Here's an edited transcript of our conversation:

StyleList: In terms of style, for men in America, are there a few people you see carrying the banner?
Glenn O'Brien: You know it's funny because every year I get this ballot for the International Best Dressed List, run by Graydon Carter. Everybody on it is an actor, or a musician or some socialite. But what interests me are people who aren't celebrities who look great.

StyleList: Like what catches Bill Cunningham's eye?
Glenn O'Brien: Right – one person who always looks fantastic is Ornette Coleman. He's in his 80s now and he still looks amazing. He's not afraid to wear color, so he'll wear, like, a green suit. Jazz musicians always look good, except maybe in the late '60s or early '70s when they decided to look like hippies.

Glenn O'Brien, Kanye West and Amber Rose at Narciso Rodriguez's Fall 2009 show during Fashion Week. Photo: Andrew H. Walker, Getty Images for IMG

StyleList: How do you think men are doing now? It seems like artists like Kanye West are leading the way, sporting A.P.C. and other fashion-conscious labels.
Glenn O'Brien: I think things are looking up again. I like what I'm seeing now. It seems like trial-and-error is starting to pay off. Fashion and arts are in a sort of parallel with food production -- it seems like we're realizing that this industrial, mass production that started towards the end of the '60s isn't going to pay off. Maybe we're ready to go free range again.

StyleList: So how did it get so bad?
Glenn O'Brien: Men had become fearful about getting noticed, and then we realized that you can't count on anything anymore. The government doesn't have your back. The unions and companies don't have your back anymore. And men have been really afraid of looking feminine; they've been really focused on looking masculine. I think now, thanks in part to gay liberation, they have more room to experiment. But media centers like New York and Los Angeles are generally always okay. Things touch off from here, and the message and fashion and culture spreads across the rest of the country, except to some really backwater places I guess.

StyleList: What about in groups of people who aren't known for their style. Any politicians?
Glenn O'Brien: Politicians uniformly look bad, because they want to look like businessmen but don't want to look too rich. John Kerry flirted with looking like a rich CEO, but they all go for that middle-American, white button-down and baggy suit look.

StyleList: John McCain wore a V-neck sweater and everyone made fun of him and called it his "gay sweater".
Glenn O'Brien: Well, also, wearing a sweater accentuates your physique more than a suit, so it wasn't really a good idea for him.

StyleList: It's been quite some time since Interview and TV Party. Has it been interesting to see the Style Guy expose you to a new generation of men?
Glenn O'Brien: It never would have occurred to me to write an advice column, but someone asked me to do it and it's turned out to be fun, and the readers do half the work. But what has interested the most has always been writing essays, and this book gave me a chance to write some essays.

StyleList: What else are you up to these days?
Glenn O'Brien: I've been writing a memoir, very slowly and lazily, because I knew a lot of interesting people and I was in a lot of interesting places. I'm still writing about art and making TV commercials. I just did a really great spot for Dolce & Gabana with Jean-Baptiste Mondino and Scarlett Johansson. It's kind of an exciting moment because for years I've been doing these 30 seconds here or there, and now we get to do these longer versions for the iPad or for YouTube. You know, I started out in film school and I got kind of side-tracked into magazines, but I did "Downtown 81," and I wrote a script for a film about Andy Warhol that I'm trying to get produced, because in the same way that I got "Downtown 81" finally done because I got pissed off about the Julian Schnabel Basquiat film, I'm kind of pissed off about the way that Warhol is depicted in several films. He's worthy of a film that's about him.

StyleList: Why do you think everyone wants to reduce Warhol down to this unfeeling megalomaniac? Is it just an easy story to tell?
Glenn O'Brien: Yeah, it's an easy story to tell. The idea that he was exploiting the people is so silly -- they never would have been in the movies otherwise. He was taking people with talent and giving them some exposure. Also, I think our culture likes to have a gay villain. It's like Dr. Smith on "Lost in Space."

StyleList: Do you see this dilution of culture affecting our music as well?
Glenn O'Brien: I've been accused of being an old fogey, but I just really don't think this is a good moment for music. There are a lot of reasons for that, there aren't very many good venues. I think hip-hop was kind of a bad influence because when you start thinking of the turntable as a musical instrument, it puts a dent in virtuosity. When I was a kid there was a local music scene -- the Motown sound, the Chicago sound, the Philly sound, even the Cleveland sound. Now that only exists in maybe New Orleans and certain places in Texas.

StyleList: But isn't that something that's been a key part of hip-hop, the allegiance to your hometown?
Glenn O'Brien: Yeah it's true. You know I ran into James Murphy a couple of weeks ago at a party, and I love LCD Soundsystem, but he was just so over it. He said he hated it, the traveling, the touring. That's the only way they make money.

StyleList: Going back to magazines, how do you feel about this moment for media? What does the future hold for magazines?
Glenn O'Brien: I just think everything is in this stage of being redefined. I don't want to say anything bad about Newsweek or whatever, but it seems obvious to me that the Internet is a better way of delivering time-sensitive material and giving you the news. So it seems like that's going to keep moving away from paper, but I think magazines will stick around as luxury items. Fashion magazines are all about fantasy, and printed fantasy is probably better than online fantasy -- although online pornography seems to be doing pretty well. And the Internet empowers people creatively so that you don't have to suck up to some publisher, you don't have to fuck someone to be visible.

StyleList: You've been a downtown New York icon for so long. Is it odd to see the resurgence here?
Glenn O'Brien: I like to see the revival. Some things strike me as odd, like when they had this thing about having artists paint storefronts on the Bowery. What's great about the Bowery is that it's the last fucked up street in New York City. It's the last one that makes no architectural sense. I was amused when Giuliani took credit for driving the crime out of New York. It's much simpler in reality -- criminals couldn't afford to live here anymore. They'd have to commute to work if they wanted to mug you in Manhattan.

StyleList: And when it comes to art, how do you see this shift to mass creation and selling? It seems like back when you and Jean-Michel [Basquiat] were friends, that's how people acquired contemporary or modern art. Nowadays there's the Broads and the Gagosians who seem to just find artists and buy as much of their work as possible.
Glenn O'Brien: Yeah, it's not good for art. It's so seductive, especially when you're young, to go for the big money right off the bat. The dealers do these museum-quality shows, so it's great for New York in that way. I just think sometimes young artists can be too impulsive. I hate the thing in the art world where things are sold by the square foot. The giant works, where are they going to hang? Some house in the Hamptons? It's too big and it'll be obsolete in 10 years. It just doesn't make sense.

StyleList: Your former colleague at Interview, Fran Lebowitz, talks about how she feels AIDS wiped out the top tier of New York artists. She says Andy would laugh if he sees who was making art now.
Glenn O'Brien: Well, Andy didn't think she was funny anyway.

StyleList: Your no. 1 style tip?
Glenn O'Brien: I just like it when you can see that a little bit of thought went into what someone's wearing. I guess I could be glib and say tuck your shirt in and tie your shoes. And don't let me see your underwear.