Whether you opt for the straight fold, the winged puff or the two-point—and be sure to Google endless others (with easy directions), because there’s a pocket-size movement at your fingertips, fellas—it’s hard to go wrong pairing the crisp, classic accessory with a handsome jacket. Beyond the fold, which particular square should you land on? “A nice pop of color goes a long way,” says Harbor East tailor Christopher Schafer, who hand-picked these stylish summer looks with his son and business partner Seth. “If you’re wearing lots of solid colors, go for a more adventurous pattern. With a very busy suit, tone it down with a simple square.” OK to wear a pocket square without a tie? You bet, Christopher says. Without a jacket? He pauses. “No, don’t do that—looks like you’re trying too hard.” Christopher Schafer Clothier, 1440 Aliceanna St., Harbor 410-404-5131, christopherschafer.com