Hideo Wakamatsu polycarbonate trolley, leather weekend tote, leather suitcase, Longchamp leather bag, and Want Les Essentiels de la Vie cotton weekend tote

Photograph: Anna Knott

Clockwise from top: Hideo Wakamatsu polycarbonate trolley, $255, Flight 001, 1133 N. State St. Leather weekend tote, $658, Coach, 625 N. Michigan Ave. Leather suitcase, $3,200, Louis Vuitton, 700 N. Michigan Ave. Longchamp leather bag, $830, Bloomingdale’s, 900 N. Michigan Ave. Want Les Essentiels de la Vie cotton weekend tote, $395, nordstrom.com.