Dave Fogg, 42

Program Director for the N9ne Group

Style icons: Steve McQueen, Ozwald Boateng, George Best and Led Zeppelin

What he’s wearing now: Rialto vintage sunglasses, John Varvatos jeans, shirt, belt and sandals

The first thing Dave Fogg thinks about when he goes to get dressed is context. “If people think of me as well-dressed … that’s amazing,” he says, with a twinge of his trademark dry sense of humor. “As long as they don’t think of me as a son of a bitch.” The self-described “alpha nerd,” says there is one thing he never leaves home without. “My prescription glasses are an essential accessory.”