The question I get asked the most about clothes is, “What is the first suit I should get?” The answer is simple: a navy or gray single-breasted suit with two or three buttons. This also leads to the second most frequent question: “What is the second suit I should get?” To which the answer is simply, “Whichever one you didn’t get the first time.” But after that you get into territory where a guy needs to think about what he wants to wear, not just what he needs in his wardrobe. So when we start talking about the third suit, we start talking about personality, pattern, and confidence. Not every man can wear a navy suit with a windowpane pattern—like this one from one of Italy’s most respected suit manufacturers, Belvest—but the man who can looks damn sharp when he does. Whether it’s your third suit or your fiftieth, it only works if the fit and fabric are beautiful. So take notes from this one here…or just take it home. Either way, you’ll be the one guys start asking for style advice.

Belvest, Brioni, Borrelli, and Lorenzini, on sale today at noon ET on Gilt MAN.

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