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The Frequent Flier
Go beyond suits and ties with an expandable bag that makes space for board shorts, casual button-downs, and other after-hours essentials.
Hideo Wakamatsu tarpaulin carryon, $225, at Flight 001, 1133 N. State St.; 312-944-1001, flight001.com.
Jack Spade printed bill holder, $145, at Jack Spade, 47 E. Oak St.; 312-915-0315, jackspade.com.
Steven Alan baseball cap in purple houndstooth, $120, at stevenalan.com.
WANT Les Essentiels de la Vie leather iPad case, $295, at Barneys New York, 15 E. Oak St.; 312-587-1700, barneys.com.
Photography: Courtesy of vendors