• Oliver Parini
• Lenny's Shoe & Apparel

Lenny's Shoe & Apparel — Lenny’s official slogan is “We fit you right,” but it could just as easily be “Well-heeled and plenty of sole.” Since 1990, the family-owned and -operated stores in Williston, St. Albans, Barre and Plattsburgh, N.Y., have been go-to destinations for fellas’ footwear ranging from sandals to sneakers and slippers to muck boots. Then, in 2011, Lenny’s employees took to the streets of central Vermont and handed out free sweatshirts and pairs of Carhartt pants to flood victims of Tropical Storm Irene. Not surprisingly, they’ve been a Daysies “shoe-in” for best men’s shoe store for four years running. Talk about toeing the line.

Other Finalists

• Danform Shoes
• Old Gold
• Outdoor Gear Exchange
• Warner Supply