1. DRESS TO GO ANYWHERE
My style is really about merging different worlds. For a long time I dressed in a hip-hop style, with baggy clothes, and then I drastically changed from hip-hop to Wall Street—I’d wear pinstripe suits and suspenders.
Now I think my personal style is being ready for an elegant dinner party but comfortable enough to wear the same thing walking on a Saturday afternoon in any city.
2. FIND A STYLE SIGNATURE
I’ve been wearing a hat for the last 10 years. Every day. The only people who have seen me without a hat
are the few people who I’ve broken bread with in a formal restaurant.
When it’s all said and done, it’s the little details that express personality. It’s what’s on top of the basic uniform—the pants, the shirt, the shoes. The hat is an accent, the socks are an accent, the jewelry. You can wear a navy blue suit and be like everyone else in the room, but the hat and the socks are going to make you stand out. I own at least 50 pocket squares, and at least 45 hats.
All of my favorite pieces have meaning. I have a big green jade ring that’s my wedding ring. I went to a jeweler with my wife, and we both pointed at the same ring. He had only made two of them, and one fit her and one fit me.
3. KEEP EVOLVING
I would never wear that anymore. It might have been right for me at the time, and I still love color, but I might not wear that combination anymore. Right now I prefer softer colors—what you might associate with the colors of Italy. I’ll still do green, but a different green from what I wore three years ago.
I don’t dress for other people, but I remember being on the train the other day, and this woman said to me, “I see you on the train every day, and you always make me smile.” It all comes back to being comfortable with yourself as a person.