Twice a year, the streets of Florence are flooded with hordes of dapperly dressed dudes who gather for the pinnacle of fashion season, at least as far as menswear is concerned: the Pitti Uomo trade show. Everywhere you look, each man is more impeccably groomed and more expertly tailored than the last. We took to the streets to glean a bit of street style inspiration, and below you’ll see a few of our favorite looks from the week. Scroll on for unexpected pairings and lessons in how to pull off the double-breasted jacket, then head over to to get the look for yourself.

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