Leather messenger bag, LACOSTE leather slip-ons, Aviator sunglasses, alligator wallets, suede brogues, canvas belt, pebble leather travel kit, and suede desert boots

CLOCKWISE FROM TOP: Leather messenger bag, $995, at Tiffany & Co., 730 N. Michigan Ave. LACOSTE leather slip-ons, $85, at Akira, 1837 W. North Ave. Aviator sunglasses, $435, at Oliver Peoples, 941 N. Rush St. Alligator wallets, $495 each, at Tiffany & Co. Suede brogues, $240, at Ted Baker, 1009–11 N. Rush St. Canvas belt, $29.50, at J.Crew, 900 N. Michigan Ave. Pebble leather travel kit, $98, at Coach, 900 N. Michigan Ave. Suede desert boots, $198, at kennethcole.com.

 

Photograph: Jeff Harris