Credit: Courtesy of Lenny's Shoe & Apparel

Lenny’s Shoe & Apparel — Whether your style is professional, laid-back or adventurous, this shop has a head-to-toe look to fit. Find rugged New England brands such as Carhartt and the North Face, as well as a timeless selection of flannels.

Other Finalists

  • Harbour Thread
  • MK Clothing
  • Outdoor Gear Exchange

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