(Credit: Getty)

(Credit:Getty)

My neighbor Sebastien Sergeant taught me that even the most basic clothes look great when the color and fit are right.

I regularly stalk the Ralph Lauren employees outside the corporate headquarters on Madison Avenue, and it's rare that I see even one that's out of step with the rest. They've mastered the art of casual style.

I have to confess that I was disappointed when it became evident that Roger Federer (as opposed to, say, Andy Roddick) was going to be the next tennis star. I didn't think I'd be able to look past the ponytail, the steely Swiss reserve, and the mundane clothes. But for the first time this year, Roger caught my eye both on and off the court. He made some bold sartorial choices--walking on court in an all-white suit at Wimbledon and blowing past Novak Djokovic in unconventional head-to-toe black at the U.S. Open--but they worked for me. And off the court he kept it simple with understated suits and open-collared shirts and a much improved shorter haircut. He is transformed--and I am convinced.

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Blake Mycoskie, founder of Tom's Shoes, looks quintessentially American in the most unpretentious way. I'd bet he wears the same clothes for days in a row. I like that in a guy--he just doesn't care that much, but he happens to look great.

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You might think I'm being just plain sycophantic for choosing Men's Vogue editor Jay Fielden as a best-dressed choice. But if you saw him as often as I do, I bet you'd make the same case. He's particularly good at picking out classic clothes in unexpected and often risky colors that only he (with his rust-colored head of curls) can wear.

Sam Buffa, a proprietor of the Freemans Sporting Club (and barber shop), gets my vote for the guy who does the whole downtown-hipster, retro-classics look best.

Photographer Charles Thompson brings something new to the typical New England "boarding-school guy." He has all the preppy hallmarks--denim shirts, plaid-lined outwear, and traditional suits--but it's his more sophisticated additions--the gold crucifix around his neck, his vintage Steve McQueen Persol sunglasses--that make him an original.

I wish I had more pictures of this perfectly dressed Mystery Man. As I said on my last blog, he is the sharpest dresser I saw on the street last year. All he told me about himself is that he is from Queens--but I did find him in my neighborhood so maybe I'll see him again...

Maybe its the resistance I have to the familiarity of mundane preppy that makes me so excited when I see someone doing it in an interesting way. Wes Anderson does it best. Hands down. If it's possible to be minimal preppy, he would be the definition.

(Credit: Getty)

(Credit: Getty)

(Credit: Getty)