$198,
at Sperry Top-Sider

An Easy Fall Shoe

Even though he's known as a retail king and the namesake behind New York's and Atlanta's fashion-forward Jeffrey shops, Jeffrey Kalinsky is a Southern gent who appreciates simple sartorial classics. Case in point: his successful collaboration with storied shoemaker Sperry Top-Sider. Kalinsky modernizes iconic styles ever so slightly—updating fits, finishes, colors and leathers—while keeping all the good stuff that has sustained over the years. This fall, he's taken a moccasin boot (not unlike a wallabee style) and slimmed down the silhouette, rounded the toe a bit and finished it in three shades of suede. It is, of course, grounded by a comfortable, shock-absorbing signature Sperry sole. Sure, you pay a little more for the limited-edition nature of the shoe, but in our opinion, they're worth it.