When we asked what Glenn’s least favorite thing about fashion and style was, his response was characteristically direct: “Mindless desperation and cultural cluelessness.” His wit, wisdom, and connoisseurship of everything from the time-honored virtues of the Belgian loafer (he owns fifteen pairs) to an admiration for how Jerry Lewis dressed on The Tonight Show to, today, the music of the Wu-Tang Clan made Glenn a central component of the New York scene in the early ’80s. Among many things, he has been a stand up comic, wrote and produced the film now known as Downtown ’81 starring Jean-Michel Basquiat and was part of the team at the early days Interview Magazine with Andy Warhol, where he wrote a column about anything he wanted to, called “Glenn O’Brien’s Beat.” Of his mentor, Glenn says, “he would not look at the magazine until after it was printed… Just to see how he operated was more educational than college and grad school put together.” While Andy was all about breaking molds, Glenn redefines them when it comes to men’s clothing. As GQ’s “Style Guy,” he knows just about everything there is to know about “the rules” – most importantly that rules are meant to be broken; you have to know how to speak the language before you can start cursing in it. Rule #1, though, is “tuck in your shirt” – untucked shirt tails under jackets, Glenn says, are a move best left to Mick Jagger and Woody Allen on his better days. While his mother warned him that blue and green didn’t “go” together, he thinks it’s a great combination. Glenn proves his point, pairing his navy suit with an emerald green Hermès tie and green Paul Smith socks – socks, he says, can match your tie or they can match nothing at all, just as long as they don’t scream. His Breton-striped Saint James socks do not overshadow, but add the perfect touch, to a paisley Etro shirt and Adam Kimmel blazer. According to Glenn, “Guys think, if I wear a Steelers jersey, I’ll look like a man.’ But that doesn’t really work; you just look like one of the crowd.” Confident in his signature Ralph Lauren saddle shoes, he says, “I dress the same as I did when I was 12, 18, 25, and 35– I haven’t had too many ‘aberrations.’” Glenn stops short of casting himself as a modern day Cicero, but relates to a fellow “wiseguy” who could never resist speaking his mind, albeit one two thousand years removed. Cicero was an orator, an intellectual, and a philosopher from a time when it wasn’t “unmanly” to use your brain – and a sometimes-soldier who wasn’t afraid to get his hands dirty – he probably would have approved of the raw denim and sailor stripes that comprise Glenn’s “Summer fatigues.” However, Cicero’s big mouth eventually got the better of him – or, at least, Mark Antony’s soldiers did – but so far Mr. O’Brien has avoided such a fate. As a former stand-up comedian, he knows that being funny and humane, in addition to being brutally honest, goes a long way. Having reinvented himself as a sort of Cicero for the 21st century, Glenn’s set his sights sharing some virtus with the modern man, both in his GQ column and in his book, simply titled How To Be A Man – “a philosophy book disguised as a humor book disguised as an advice book.” Nevertheless, as unable to resist a ripe wisecrack as old Cicero was, he says his favorite thing about fashion is, “Two women at a party, wearing the same dress– horrified.” If you love Glenn, you may also like Susan Blond, Waris Singh Ahluwalia and Daniel & Steven.