Cigar Aficionado

You can now include a wide spectrum of color and pattern choices to the many attributes of the boat shoe. That venerable piece of footwear that pairs nautical purpose with undeniable panache is branching out from its one-style-fits-all roots. While improving on a great design may be difficult, shoemakers are proving you can sure jazz one up.

Paul Sperry created the modern boat shoe one winter in the 1930s when he observed his dog holding traction while running on the smooth ice of a Connecticut pond. On closer inspection, the dog’s paw revealed hundreds of tiny, gripping fissures, which were the inspiration for the deck-hugging soles of the Sperry Top-Siders, the archetype of the style.

What began as functional footwear went on shore leave and became flippant fashion. The East Coast prep school crowd kicked around in the sea shoes on an everyday basis and made them a sole staple for summer wardrobes—one of the few things we can thank them for.

Wear them casually, with shorts or jeans, or dress them up with slacks and a bow tie for an affected Southern-preppy look. Just leave the socks folded in your drawer lest your shoes be mistaken for loafers. And sailors should never be modest about allowing this work shoe to do its job; time in the saltwater and sun confer authenticity.

The Allen Edmonds Harbour (top, shows the classic chocolate brown look, but it also comes in a palette of colors. For a walk on a wilder side try the blue kicks from Brooks Brothers (second from top, They have perfected the tradition with simple stitching and a quality material that will age well, on sea or shore. And boat shoes are equally sturdy in canvas, as demonstrated by the Coastal Springs 2 Eye from Rockport (third, and the Oliver from G.H. Bass (fourth, with rough-stitched red and a green variation with three rows of lacing eyes instead of two. And Sperry Top-Sider represents their New England prep origins with the Salt Stained Boat (bottom,, a three-tone leather that catches eyes without losing simple elegance.