Ballerina flat meets sneaker in this rubber-soled slip-on with playful details.
Elie Tahari, $148; 212-334-4441.
Striking linen and leather lace-up has an insole with a double layer of latex foam.
Glory Chen, $275; 212-677-2938.
Classic all-American sneaker, reinvented in navy and slicked with a patent leather toe. $49; Talbots.com . Steal his style with smart-looking classic oxfords