Chicago Premium Outlets
Credit: Jean-Pierre Lescourret / Getty Images

Unsurprisingly, the Windy City's outlet mall offers clothes that handle the cold. Pick up long underwear at Jockey or Hanes, tough boots at Timberland, or a cashmere cardigan at Banana Republic before exploring your coat options. Once you've got the basics covered, you can check out the colorful toggles at Benetton, classic sportscoats at Michael Kors, techno-fabric mashups at Calvin Klein, and upper-crust overcoats at Ferragamo. [Chicago Premium Outlets; 1650 Premium Outlets Boulevard, Aurora, IL 60502]