New Wave Boat Shoes: Nothing wrong with traditional brown boat shoes, but with everyone from Sperry to Gucci doing creative new riffs. Patterned Pocket Squares: By now you've caught on to the 1960s Mad Men pocket-square thing—and so has everyone else. Stay a stride ahead by mixing plaids and checks in your rotation. Just be sure to pair them with solid shirts to avoid pattern overkill. Plastic Aviators: Wire-framed aviators have been a stone-cold classic for decades—now they've gotten a timely update. This new riff co-opts the chunky plastic cool of Wayfarers and applies it to the timeless fighter pilot's silhouette. Straw Fedora: Dressing seasonally applies to your headwear, too. That means going with a straw—not felt—fedora come spring and summer. The coolest version right now is known as "stingy," in reference to its super-narrow brim. Brightly Coloured Faces: Even if all the dudes at your office have thrown a chunk of cash at an impressive watch, they probably don't have one quite like this. A red, blue, or green face will add a shot of badass-itude to your otherwise conservative business look.