1. Leather and fleece-lined sneakers, $95, Vans, 39 S. State St.
2. Leather and cotton sneaker boots, $1,540, Louis Vuitton, 919 N. Michigan Ave.
3. Elastane and polyester technical knit sock sneakers, $245, Sandro, 102 E. Oak St.
4. Givenchy leather, mesh, and thermoplastic polyurethane low-top sneakers, $925, Neiman Marcus, 737 N. Michigan Ave.
5. Burberry cotton, leather, and rubber low-top sneakers, $390, Bloomingdale’s, 900 N. Michigan Ave.