Elie Tahara slip-on shoe

Ballerina flat meets sneaker in this rubber-soled slip-on with playful details.

Elie Tahari, $148; 212-334-4441.

Glory Chen linen and leather lace up

Striking linen and leather lace-up has an insole with a double layer of latex foam.

Glory Chen, $275; 212-677-2938.

Talbot's classic sneaker

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