Esquire’s Best Dressed Real Men in America 2009: Meet the Finalists


Ontario Armstrong, 27, Entrepreneur, Philadelphia
How he won: By taking chances. “I throw so many things out to the wind, from my suits and socks to my shirt-and-tie combinations.”

But here he’s wearing: “I got this suit custom made for $400 in Vietnam, and I’m big on what I call ‘tricky socks.’ Just to give the outfit that extra wow.”

A man can never own too many… “Shoes. There is no such thing as too many shoes.”


Dan Trepanier, 22, Student, New York City
How he won:
By being named “fan favorite” by online voters and by dressing the same way he played basketball at Columbia University: “You never want to blend in. You always want to shine.”

But here he’s wearing: “A basic white shirt — can’t go wrong with that — and a rugby shirt that’s bold only in the sense that it’s red and blue. Everything else is toned down. You should have only one bold item per outfit.”


Santino Lattimore, 34, Real Estate Agent, Atlanta
How he won:
By listening to his mother. “My mom was a buyer at a retail store, and she always stressed that you should present yourself with your gift wrapping on. The true gift lies inside, but you have to present yourself really well.”

But here he’s wearing: “My casual look. I try to create a fashion statement every time I dress, and I like taking things that don’t look like they belong together, like this jacket and scarf, and making them work. It’s an art.”


Matthew Fan, 27, Lawyer, New York City
How he won:
By not overthinking it. “I’m not a very fashionable person. I built my wardrobe in such a way that I don’t have to think that hard in the morning.”

But here he’s wearing: The same thing. “This is how I dress 90 percent of the time. Whether I’m going to work or whether I’m going to dinner, a sport jacket and a tie are almost always appropriate.”


Kevin Kasson, 18, I.T. Consultant, Coralville, Iowa
How he won: By keeping it classic. “I used to wear jeans and T-shirts every day, but then I started watching old movies. The white dinner jacket in Casablanca is what got me to start dressing well.”

But here he’s wearing: “I got this suit on eBay. It’s unworn from the ’50s, and it’s made from a sharkskin sort of fabric. It’s a little shiny, but from far away it looks like a standard medium blue.”








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