A Sperry is a type of shoe that preppy rich kids wear. Not all Sperry's symbolize "rich" though. There are many different colors for girls to choose from, and those shoes are only around $50, which isn't much. To know who your true Sperry Ritz are, it's the girls or guys that wear Sperry's that are completely plain - they're usually a tan color. They are typically for boating, although many non-boaters purchase them. They show class and style. People who wear Sperry's are people you should worship, because who else pays over $100 for shoes that will be ruined if you even get them wet?
Joe: "Hey Luke I see you're on that Sperry's grind today!"
Luke: "Yeah, my dad is CEO of a bank now so why not."