We preppies love our loafers. Our mummies kept us in lace-ups until puberty, and the slip-ons (Bass Weejuns, in my case) gave us our first taste of freedom. They’ve been a staple for non-preppies, too: James Dean sported a pair with cuffed jeans, while Michael Jackson wore his to moonwalk. Now, Cole Haan is taking them to a new level. For its 80th anniversary, the company reimagined its original loafer in a range of styles, from hand-sewn moccasins to high heels to a patent-leather pair with just the right amount of shine. Add their secret weapon—a cushioned insole developed by Nike—and you’ll feel like you are floating above the ground, smarter than the average pedestrian wearer. Plus, these beauties can go the distance: long walks through Central Park, down Regent Street, even around the Bois de Boulogne. And, like their wearers, they’ll only look better with age.