It makes sense that men would like slip-ons: Why fumble with laces, straps, and zippers when you can just slip your foot in and get on with life? Not surprisingly, laceless shoes have been around for centuries. Native American moccasins predate Columbus' discovery of America. But the genre of footwear has evolved considerably, and they're not just for casual occasions, either. Here are the five classic brands associated with each style—driving shoes, boat shoes, loafers, Vans, and slippers—and how to wear them. One tip is consistent: Lose the socks.
BOAT SHOES (TOP-SIDERS OR DOCKSIDES)
A boating enthusiast named Paul Sperry invented Top-Siders (pictured) shoes in 1935—he was inspired by the way his dog's paws never seemed to slide on slippery surfaces. The U.S. Navy then started manufacturing the shoes in 1939, and today, of course, they're a preppy staple. An alternative was born in 1970 when Sebago launched Docksides.
Best worn with: slim rolled-up chinos and a plaid shirt.