Credit: Davies + Starr

In 1935, Paul Sperry invented a pair of shoes that wouldn’t leave scuff marks on his deck—and the Top-Sider was born. The image of JFK wearing the white-soled oxfords on his sailboat elevated them to an American classic. Now Sperry Top-Siders (; $85) come in colors like red and blue. Best of all, they’re ideal for travel—both on land and off.