Allen Edmonds

Wingtips have always been on the casual side of the dress shoe spectrum, but footwear legend Allen Edmonds has nudged the style into more aggressive territory with their Special Edition Kasmuk ($300). The striking blue denim uppers are definitely a step outside of the company’s typical brogue comfort zone.

Men’s fashion authority Allen Edmonds knows a moneyball when it sees one. The Fastball Boat Shoe ($115) adroitly struts the tightrope between gimmicks and licensed apparel to create a unique set of boaters for fans of America’s favorite pastime.