Shop Now $1,050, gucci.com There may be a few contenders—bucks and boat shoes spring to mind—but there’s a strong argument for the loafer as the quintessential preppy shoe. No wonder ...

Best luxury: Gucci Brixton Horsebit Convertible ... as well as those that specialize in walking shoes, to find styles of loafers that meet somewhere in the middle. Any shoes that felt noticeably ...