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.
Dressing seasonally applies to your headwear, too. That means going with a straw—not felt—fedora come spring and summer.
Brightly Colored 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.Breitling $2845
New-Wave Boat Shoes
Nothing wrong with traditional brown boat shoes, but with everyone from Sperry to Gucci doing creative new riffs, why not go for something more up to date than the ones JFK sported? Try a streamlined new silhouette or a splashy color instead.
Band of Outsiders for Sperry Top-Sider $200
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.
3.1 Phillip Lim