When most people think of Sperry shoes, the Top-Sider probably comes to mind first. The white-soled leather "boat shoes" have become synonymous with leisurely prep style, although they were made with sailors in mind. Paul Sperry’s patented, non-slip, "siped" soles (designed so you wouldn't go flying off the deck of a sailboat) were so effective they were even commissioned for the U.S. Navy in WWII. But these weren’t the first shoes Paul Sperry put out. That title belongs to the underrated CVO, or Circular Vamp Oxford.

The simple plimsolls were reminiscent of Keds canvas shoes (and predate Vans by a few decades), but offered surer traction in wet conditions. The Top-Sider, which came later, utilized tanned leathers that could better withstand exposure to salt water, but we love the CVO both because it predates the Top-Sider, and because it offers similar functionality in a crisp sneaker silhouette.

The reason boat shoes (like the Top-Sider) and deck shoes (like the CVO) were adopted by preps was simple: Both models lent themselves to a lifestyle that prized being outdoors—often on the water—and were practical shoes with an understated appeal. It's no coincidence that the aesthetic caught on, and that shoes originally designed for sailing on Long Island Sound have become go-to summer kicks around the world. You can buy boat shoes and deck shoes from almost any brand these days, but you’d essentially be buying a pair of knock-off Sperrys.

This year's Noah x Sperry collaboration includes a brightly color-blocked leather Top-Sider and two versions of the canvas CVO sneaker—one in our all-over "SOS" print with red, white and blue laces, and a second in patchwork nautical tones. We've also included a long-sleeve tee, six-panel hat, canvas tote, and beach towel employing their classic Cloud logo.