Glenn O’Brien’s position in the cultural firmament is, at this point, unassailable. He’s defined his unique place in the world and no one can claim it from him. But just because there’s not much left to be said about Glenn doesn’t mean he doesn’t have a lot to say himself. His new book, How To Be A Man, comes out later this month. It’s a collection of indispensable essays on everything from beards to snobs, wine to women. In a world suffering from information overload his words, stylish and irreverent, cut to the heart of the matter.

We spoke over a leisurely lunch at Il Buco. Interview by David Coggins.

David Coggins: How did you come to the idea of writing the book, and why now?

Glenn O’Brien: Well, The Style Guy column has a big audience, and I thought I should write a book for that audience. But I didn’t want to do a greatest series of Q & A’s, so I thought it was a perfect opportunity to write some essays. Basically this is all original, I mean there’s a couple of things that appeared here and there in slightly altered versions. But most of this is original, although I did cannibalize a lot of good lines.

DC: Is there some particular moment now that people are asking or asserting how to be a man–is it all these lumberjacks going around with beards?

GO: Don’t you like that? I think we’re at a pivotal moment, I think the yang is returning.

DC: And how do we see that? People certainly care where their clothes are from are how they’re made.

GO: I think culturally we reached a point of the sort of nadir of wussiness, and I think that people are going to be a little more assertive and demanding, and individual. Don’t you think?

DC: I think so. There are many more options for people to express themselves in a way that’s smart. But you talk about casualization of dress. Are we still suffering from that? It feels like we are.

GO: Yeah, except I think the casual is getting dandified, which redeems it somewhat. I don’t think we all need to go back to wearing suits and ties all the time, but I think just not being in the sort of generic uniform is the point. People now realize that they have to be entrepreneurs, because there are no jobs. If there was a job you wouldn’t want it, because you have to be such a tool to do it, and be completely amoral, and personality-less.

DC: In that regard, people can dress for the job they want, or the way they romanticize that job. You express your ambitions by the way you present yourself to the world.

GO: Right. You start out as a phony and become real.

DC: When does that happen? You never know until you look back and you realize it’s already there. You have some funny things to say about Pat Riley–he’s an example of that. It’s like his attitude, the way he dressed, his thoughts about winning–his look expressed pure capitalism somehow.

GO: Yes, and the teams were tremendously successful, and it was LA, and he was bronzed, he had that hair slicked back. He looked like a hood ornament on a car. And he was Mr. Armani.

DC: There was something about this very, kind of refined dress on the sideline, contrasted with this incredibly physical activity on the floor in front of him. It’s trying to make order out of chaos, fifty feet away. By men much taller than he is.

GO: I remember, there was a great fight, that the Knicks were involved in, I’m trying to remember what the other team was. I don’t think it was Pat Riley, I think it was Jeff van Gundy.

DC: It was the Heat, with Alonzo. Right? And Jeff Van Gundy’s holding around his leg.

GO: That’s it. And Greg Anthony is a pretty well-dressed guy. But he was wearing the ugliest sweater that day that I’ve ever seen.

DC: Was he on the sideline?

GO: Yeah, he was hurt.

DC: Hysterical. So he was in his civilian clothes. He’s not a bad analyst.

GO: He’s a really smart guy. I think he was like the head of the Young Republicans at UNLV.

DC: But you also say that in retrospect those padded Armani suits are some of the things that you regret wearing.

GO: I guess we needed it. We needed to feel strong. To me it really looked silly on athletes. If you have big shoulders, like Michael Jordan or Howie Long, it just makes you look like you have a peanut for a head. It’s funny, because I actually had a couple of Armani Black Label suits, and they were beautiful fabric, and I took them to a tailor, to see if there was anything that could be done, to see if you could remove shoulders. And there isn’t. So they’re probably being worn now in Zaire.

DC: Suits seem to have changed. I like the idea that a man can be rebellious in a suit. It doesn’t represent your affiliation to a corporation, it’s more about self-expression. In a weird way, the more conservative it is, the more unexpected it is.

GO: Yeah. I love suits. I have to get new suits, I realized last night.

DC: What happened last night?

GO: Well I lost some weight, and generally suits have gotten more form-fitting. So most of my suits look too big now. Plus after the Thom Brown influence of like, the shorter jacket.

DC: There’s a good new tailor on Greenwich Street, called Miller’s Oath. Kirk Miller is a young man who works with a tailor, from a pattern he cuts. He makes beautiful suits and tweed sport coats. It’s good thing to have a personal relationship with a tailor in the city.

GO: It’s really hard to find a good tailor. I like the idea of Thom Browne, and I like the way it looks on people, but it just doesn’t work for me. The pants don’t fit me. Oddly it’s the waist that doesn’t work, I don’t know why.

DC: You have a chapter about dandies. You write about it being quite bold, like Belgian shoes. Like asserting yourself by getting close to your feminine side.

GO: Yeah. I like faggy shoes. I guess people think of dandy as effeminate, but that’s really a fop. There’s a big difference between a dandy and a fop. Have you ever read Baudelaire on the subject? For him, a dandy was a hero, it’s how to stand out as a real individual in a conformist context.

DC: And there’s more of that now.

GO: There is, but it’s not about wearing a clown suit. It’s putting your own, I hate the word spin, but putting your own spin on a standard.

DC: Right. Asserting your personality, somehow. The clothes have to serve the purpose of expressing who you are, how you see yourself in the world.

GO: You know Hooman Majd, right? Hooman is a dandy, but he’s fierce. Wearing his Savile Row suits, with his cotton, Persian shoes, dyed green for the revolution.

DC: So if you decide you need suits, what’s your plan of attack?

GO: Anderson & Sheppard is coming in May, so maybe I’ll try that again. The suit that I have now, that fits the best, is actually a really, really, old Gieves & Hawkes suit. It’s so old it has no vents in it, so it’s from that Pat Reilly moment.

DC: The Anderson & Sheppard’s house style is wonderful.

GO: It is, but they’ll work with you if you say, I’d like the jacket a little shorter, or if you’d like a more natural shoulder.

DC: It’s a lot less structured than a lot of Savile Row suits. There’s that wonderful soft rolled lapel.

GO: Yeah, and if you get it in the right fabric it’s incredible how much wear you can get out of it before you get it pressed.

DC: I have bad habits with taking suits and trousers to the limit, and getting them patched up or reseated. Sometimes I’ll go back to the tailor again and again, and he looks at me like, ‘This can’t go on any longer,’ and say, ‘I’m taking this all the way.’ At a certain point he understands, and some Russian tailor says ‘You’re very attached,’ like he appreciates it from a moral point of view. He accepted that I refused to get rid of these trousers until they withered into infinity.

GO: Speaking of tailors, you know what I realized not that long ago? You want to buy a suit off the rack. You go into Barneys, you go into Bergdorf’s, and this guy comes up with a tape measure, and his pants are totally bunched up around his ankles, his suit doesn’t fit! And this is the guy that’s supposed to make you look good, it’s crazy.

DC: Why is that? It’s often some old-timer from Sicily who’s very charming, but you also wonder, ‘Why aren’t you dressed the way the people on the floor are dressed?’

GO: I think a lot of times you don’t get what’s right, because people are afraid of them. You say ‘Well this guy must know what he’s doing, he’s the fitter.’

DC: It’s very hard to assert yourself in that situation and say ‘Shorter, shorter, I really like it short.’

GO: Well I got a ready-to-wear suit last year, and I brought it in short.

DC: Just cause that felt right?

GO: It looked better. It looked modern.

DC: When you meet somebody what gives away the fact that he’s a dandy? Do they have some unexpected accessory? What do you notice about somebody when you cross paths with a promising young person at a dinner party or an art opening?

GO: I think it’s more of the vibe. But you can tell a lot by shoes.

DC: There are a handful of classic shoe silhouettes, that have looked good for more than a hundred years and can’t really improve upon. When I see squared toes, or any footwear novelty, I get very concerned.

GO: I remember when GQ was into the square shoes, and I’m like ‘uh-uh. You’re not going to be wearing those in five years.’

DC: You shouldn’t be able to locate the year of anything.

GO: No. The one thing Ralph Lauren said to me, he said ‘If it doesn’t look right now, it never looked right.’ Of course he was wearing ski pants and an Indian sweater when he said that!

DC: I think you do find ninety perfect photos of Ralph Lauren, but the ninety-first time is a little curious. A sweater with an American flag on it or something. But that’s the exception that proves the rule.

GO: He got a lot out of the American flag sweater.

DC: What do you come up against that strikes you that you don’t like. Some people react negatively to a bowtie.

GO: Yeah, I saw that Fantastic Man has declared a fatwa against the bowtie.

DC: But if done correctly, like so many things–especially if nobody else does it–it’s good.

GO: Yeah, that’s OK. I’ve never seen those guys wearing ties anyway.

DC: Do you have any other hang-ups?

GO: Well the usual stuff. Flip-flops, fanny packs, backpacks, baseball caps, skiing clothes in the city. It’s a lack of sense of occasion. Any major sport league licensed merchandise, not in a stadium.

DC: Not in sight of the field, or the playing surface. I get into arguments with people about the bag with wheels.

GO: I finally gave in.

DC: Did you? Oh no. Because you and Andy Spade were the last people I had on my side.

GO: I broke my arm for years. Now I’ve just given in. I travel too much. I just got a really heavy MacBook Pro. I’m getting to old for that stuff, I held out as long as I could.

DC: It’s going to be very lonely for me now.

GO: Plus, when you’ve got a kid, you’ve got to put the whole family on wheels.

DC: So maybe a small duffel bag is a sign of bachelorhood, of un-affiliation, traveling under your own power, while wheels equal responsibilities, domestic life.

GO: It’s a sign of old age. In fact, I had a walking boot from when I broke my ankle, and I saved it for years, thinking ‘Maybe I’ll wear this to the airport’ one of these days.

DC: Where do you particularly like the way the men dress?

GO: Italy, Paris. London is interesting, because the men look so much better than the women. The women all kind of look upholstered. You always see something funny in Paris. Like a guy wearing a tortoiseshell headband to hold his hair back. And the Italians do English better than the English.

DC: I love the Napoli style because it’s like the more they adhere the Anglo style the more their Italian-ness shows through.

GO: I think some of the most pleasurable moments for me, have been when I’ve been stopped and asked directions in Paris or Rome.

DC: And then you feel compelled to give the answer too, right?

GO: Of course.

DC: You say a dandy may have secrets. And maybe one of those secrets is that he’s a sports fan. I’m always interested in artists who like sports. Or English writers who know much more about soccer than you’d expect them to. Even have a little bit of disproportionate fandom can be a good thing.

GO: Yeah, do you know Tim Hunt, the curator of the Andy Warhol foundation? He’s married to Tama Janowitz. Tim is a real dandy. He’s a handsome guy, he sort of looks like Peter O’Toole. Loves to drink, drinks at lunch. His suits are so wild, he’s got a great Chinese tailor, and he uses fabrics that were never intended for a suit, and he always looks great. But he’s a rabid Arsenal fan.

DC: Arsenal is a classic team of the creative class.

GO: I was in London with him, and he was like ‘They’re playing their last game at their old pitch, we’ve got to go!’ And golf, you know? Guys who know how to dress on the golf course, that’s really something. Cause most people look ridiculous.

DC: They just ignore simplicity and common sense?

GO: I used to play with this guy who was an artist, not a successful artist. His name was Derek, I can’t remember his last name. He was a good golfer. He would wear a long sleeved white shirt and a tie, and the guy could really hit the ball, but he looked great, because he looked like it was 1930, you know when people used to wear regular clothes on the golf course. I mean I don’t go that far, but I like that he did. No baseball caps that said Buick. I mean these guys look like Nascar cars.

DC: Years ago, I spent an eccentric season lawn bowling in Central Park, and you had to wear white, and white flat shoes. And I wore a knit tie tucked into my shirt and derived great satisfaction from it, because it’s hard to find a sport where you can wear a tie. Well, there’s fly fishing.

GO: I love it, when they used to wear long white flannels to play tennis.

DC: Yeah the photos of them afterward, they could be at Cannes. You see René Lacoste after a match, it looks like they’re at a luncheon.

GO: And how bad do they look now?

DC: It’s because you’ve got an athletic apparel company dictating the basic decisions they make. Of course you’re going to have trouble.

GO: You remember the NFL? Who was the coach that wanted to wear a suit, and he wasn’t allowed?

DC: It goes against their licensing agreement.

GO: It goes against the licensing agreement, so Reebok started having to make men’s suits to accommodate this guy.

DC: You can’t beat Tom Landry’s look on the sideline.

GO: Tom Landry, Paul Brown.

DC: Now you express yourself with your tattoos or your celebration dance. I miss Jerry Rice, someone who’s a dominant, thrilling athlete, and when he scored he just acted like it was inevitable.

GO: I like when they hand the ball to the ref.

DC: Yeah, no crossing themselves, no pointing.

GO: Pointing to the sky is really bad.

DC: It’s supposed to be a humble act, but it seems like they’ve got some sort of connection that the rest of us don’t have. It’s not penitent at all.

GO: Jesus said, take the Giants and the points.

DC: It’s funny that documentary, Harvard Beats Yale 29-29.

GO: How great is that?

DC: It’s so good, it totally shocked me how engrossed I was in the actual game, because they’re still athletes, they’re not three-hundred pound specialists.

GO: How cool is Tommy Lee Jones in that movie?

DC: Tommy Lee Jones, the Harvard PR announcer, the overcoats they wear on the sidelines, Calvin Hill.

GO: You know who was my high school quarterback? BD.

DC: Wow. Is that true? The man who never lost a game.

GO: I went to my interview at Yale, and they said ‘Hi, nice to meet you. Think there’s any chance Brian Dowling will come here?’ I was so depressed. I knew I wasn’t going to get in. They weren’t going to take two guys from St. Ignatius. And then I went to Harvard, and you know what they said? ‘Think Brian Dowling would ever come here?’

DC: I really liked the feeling of a college game then.

GO: I had season tickets to the Knicks for fifteen years. And I gave it up. And I will not watch the NBA now. I haven’t watched an NBA game since I gave up my tickets, and I feel so much better. I watch a lot of college games, and it’s a much better game. I love to watch Princeton play. I love to watch VCU. I felt a lot better about them beating Georgetown after they got to the Final Four.

DC: Do you have unexpected sports friendships with anybody?

GO: Yeah. Joey Votto is my new friend.

DC: Is that true?

GO: Yeah, he read my column, and before he got his MVP award, I got a call that his agent had called GQ and asked if I would speak to him. And then we started texting, and talking on the phone. He wanted to know what to wear and he only had two days, and I said, well why don’t you go up to Bergdorf’s and get a Tom Ford tux, cause I think it’ll fit you. And it fit him perfectly. We email every other day. He’s a really cool guy. His father was a chef, and his mother is a sommelier, in the best Italian restaurant in Toronto.

DC: Do you have friends that you watch Georgetown basketball with or the New York Jets?

GO: Do you know Richard Regen, Barbara Gladstone’s son? He’s a screenwriter, and we watch a lot of Jets games together. He has season tickets. Although I don’t know if he’s going to pay his PSA’s, or whatever it is. I can never remember which one is the prostate test, and which one is the one that gets you your seats.

DC: And what do we think of Rex Ryan’s addition to the New York cultural scene?

GO: I like Rex. I like outspoken, overconfident people. And he’s funny. There’s not enough people with senses of humor in sports.

DC: What are we making of all these bearded lumberjacks walking around the city? Is there going to be a backlash against that or is that just a healthful expression?

GO: I like the beards. Black guys started wearing Timberlands in the city, though that was a while ago. I like a more urban style of clothes, if you’re in the city. I have been spotted in my red plaid Woolrich jacket around town a couple of times, but usually on a casual day. And there’s something to be said for that. It’s warm. The thing about vintage is, you don’t want to look like everybody else. So you buy something old, you know there aren’t a thousand of them out there. It’s more likely to be a unique thing at this point. That’s what looked so great on TV Party. In those days there wasn’t such a thing as designer clothes, it just didn’t exist and people looked better for some reason. They just followed their instincts.

DC: Somebody mentioned that they just saw some old photos of you on TV Party and got very rhapsodic.

GO: Right, they were in GQ. I get a lot of ‘Oh, you were cute!’

DC: How are you supposed to handle that? ‘Thanks, I think?’

GO: I kind of want to break down in tears.

DC: That’s the compliment that retracts itself before you’ve even answered, right?

GO: Yeah, I think the correct answer is ‘Bend over, I’ll drive you to Newark.’

DC: I think one interesting thing that has happened for the generation in their twenties, is all these incredible photo sites allow kids to see street style at the highest level.

GO: I think the Internet is going to change everything. It’ll do for fashion what Facebook did for North Africa. You know, like, liberate us from the authorities. ‘We want democracy!’

DC: But it’s depressing when media corporations and fashion companies try to take their business model to the internet. They don’t seem to understand what the internet is good at.

GO: No, I mean if you look at it, the best things on the Internet are all done by entrepreneurial young people, you know like The Selby or that crazy girl who does Man Repeller. It’s this girl who’s like this Upper East Side, Park Avenue, Jewish girl, who’s sort of like the fashion Sarah Silverman.

DC: Right she likes parachute pants and gladiator boots. I wanted to be the exception who like those things, but often I do find them repellant. When you finish a book, do you celebrate and go on vacation?

GO: I want it to be a success, so I do interviews. And I like to talk, so why not? I got the book on a Friday, I went to Connecticut, I lay down on the bed, sort of one eye on the basketball game, I read the book. I found four or five mistakes, and it irritated the hell out of me, but basically I thought, well that was pretty good.

[How To Be A Man]