Bill Webb: 67, Retired Wall Streeter
Old man style is killer on it's own, but when it's coupled with old money it's out of this world. It's my belief that the reason older guys have style to blow is due to the fact that they couldn't give two shits about how they look. At this point in their life they know what they like and what works. This enables true nonchalance, as opposed to the contrivances we see all the time, and in turn breeds true personal style. It's weird to think that the best dressed people I have ever met don't really care all that much about clothes.
DJ Cassidy: DJ and producer
I love it when guys take preppy to the max. DJ Cassidy not only takes it to the max, but somewhere into overload territory. I'm not sure if it's his style I love or the fact that I have this awesome image in my head of a guy tearing up the wheels of steel in a kit that looks like he came straight from the Lifshitz bar mitzvah.
Josh Peskowitz: 30, freelance editor, writer, stylist and consultant
You probably already know Josh from his stint as fashion editor at the now defunct men.style.com and his role as 1/2 of the "In The Closet" team. I respect the hell out of Josh's pedigree and his signature combination of dapper gear and street wear. He's shown up in that Dries Van Noten suit before and how can you blame the guy? If I owned that suit I'd be wearing it every waking minute.
Michael Macko: Men’s fashion and retail consultant/stylist
Dude's like a mini Mark McNairy only not as cool because he's not Mark McNairy. I'm loving the genius camo details of this look, which makes the rest of his terrible outfit choices even more dumbfounding. [Editor's Note: I have since been informed by a very smart man that Macko is LEGIT so I guess I'll let some of his tomfoolery fly.]
Ouigi! “The Bearded Man” Theodore: 32, creative director of and partner at the Brooklyn Circus and BKc Men’s
Unlike a lot of people I I'm not all over the Brooklyn Circus, but then again I don't think I am really their customer base. Nevertheless, I understand and respect what those guys are doing. Ouigi's style seems authentic and to come from "the right place" so I'm cool with it. He's also got a ton of charisma, which never hurts.
[Editor's Note: Since I am not even a fake authority on women's clothes I decided to leave that breakdown for those who actually know what they are talking about.]