CAP IT: What winter hat would be complete without a customized, removable pom pom? These locally made hats—made from super lux cashmere and lambswool with a softer-than-a-baby’s-bottom thermal fleece underband, come with badass detailing like leather, plaid and cork patched designs. With names like the “Mr. Awesomer”, these hats make being warm look so much cooler. GET IT: $75; Online at P+L Chicago.