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.
These tend to be made of suede or leather and, unlike other slip-ons, have flexible soles. The Tod's driving shoe (pictured), first launched in the 1970s, is the most iconic brand; its most famous product is the Gommino.
Best worn with: white jeans, a chambray shirt, and a safari jacket.