(Photo: Jake Chessum)

You look fantastic.
If you really want to know the truth, it’s that I don’t think about it. I know what looks right on me. I found out quite some time ago that when a man becomes a certain age and tries to look young it’s really dreadful.

What looks right on you?
It’s really all about tailoring. It’s about proportion. I use this guy called Peppino—like the little mouse, you know?— on Lexington Avenue. I buy suits from Ralph Lauren or in London or at Bergdorf Goodman, and I bring them over and we figure it out. I’m only five seven and a half, but people stand next to me and say, “Wait, you’re really short; I had no idea!” and I say, “Well, it’s the attitude.”

How do people react to you?
They say, “Whoever you are, you look really great.” And I say, “Okay, fine. That’s nice.” I have been on the International Best Dressed List twice, and I’m just kind of like, “Yeah, it’s great, but so what?” Every once in a while, though, I’ll look in the mirror and see myself and say, “Oh, it is really nice how I look.” And I mean, I used to be 200 pounds.

Really? When?
When I was younger. But now I’m an avid jogger. Who wants to be fat? You lose your courage.

Did you have many other looks before settling on this one?
In the old days, I had bracelets from one end of my arm to the other end, and long hair. I loved that period, but I can’t look like that now. On this journey, you have to know when to stop and go on to the next thing. It’s like guys who are balding with skinny ponytails. I mean, come on.

Related:

• Archive: “Look Book”
• Articles by Amy Larocca
• Table of Contents: May 14, 2007 issue of New York | Subscribe!