Timberland Mag Mile’s newest shop offers more than just the typical Timberland climbing boots—although you’ll find plenty of them if that’s what you’re looking for. The company has stepped up its offerings over the years, featuring stylish men’s and women’s apparel, as well as more fashion-focused boots, boat shoes and more. Standouts include boots from the Earthkeepers Collection, stylish numbers made from recycled rubber soles. 625 N Michigan Ave (312-573-2234).

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