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.
Folks in Norway were hip to loafers way before Americans were. Various magazines covered the trend in the 1930s, and in 1936 a guy named G.H. Bass liked the idea so much he created his own version (pictured) called Weejuns, as in Nor-Weejuns. Today variations include the penny loafer, the tassel, and the kiltie (a.k.a. fringe or tongue). All have stronger soles than other styles of moccasins.
Best worn with: slim washed blue jeans and a half-tucked polo shirt.