The Italians have mastered the art of sprezzatura—appearing effortlessly put together and stylish. This seeming nonchalance is in fact the result of measured and deliberate skill in the case of a man’s suit. As any well-heeled Italian can tell you, a Neapolitan cut is noticeably different from a Milanese silhouette. Because clothing has evolved to reflect the character of the city where it is made, Italian style is as varied as its geography. Milanese discretion prevails in the north, where sober blue and gray suits are the preference; to the south, in Naples, where the jacket is a statement piece, an exquisite expressiveness meets the eye. Florence is influenced by the nearby Tuscan countryside, where men tend to wear tweed in shades of olive and rust resembling the hills, while Rome exudes cosmopolitan glamour thanks to slightly bolder suits. For the sartorially minded traveler, we map out the peninsula’s best regional tailors and other points of interest to the well-dressed and well-groomed gentleman.