Here's a relaxed O'Brien on Andy Warhol, style tribes, taking risks (i.e. looking different) and his recent advice book for men.
What I like about O'Brien's approach is his distinctive take on style. He's more open to risk-taking, seated perhaps in his experiences with the creative hothouse of the New York music and art scene in the 1970s and 1980s. But he also sets sensible boundaries for what men should or should not wear such as the dubious proposition of sporting baseball caps at non-sporting events. Agree. Like. +1.
O'Brien also describes his new book How To Be A Man as "a philosophy book disguised as a humor book disguised as an advice book". It's a very interesting approach to a potentially cliche-driven genre. A book on style advice disguised as something else. This maneuver and disguise, I think, separates the most interesting books on style from the rest.