Clockwise from top:
- Calfskin bag with removable shoulder strap, $2,380, Salvatore Ferragamo, 645 N. Michigan Ave.
- Textured calfskin bag, $1,995, Burberry, 633 N. Michigan Ave.
- Worn-in leather weekender, $475, jcrew.com.
- Diamante-patterned leather duffel, $2,300, Gucci, 900 N. Michigan Ave.
- Canvas duffel with leather base, $2,800, Bottega Veneta, 800 N. Michigan Ave.
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