Before there was Timbaland, there were Timberland boots. And before pop stars began naming themselves after consumer brands, there was the Abington Shoe Company. Established in 1933, it would eventually blossom into the $1.4 billion footwear-and-apparel behemoth now known as Timberland. Boots were cut from simpler cloth then—the only indulgence was often brightly colored laces—and most looked a lot like the limited-edition Abington Hiker. You won't find any Gore-Tex, synthetic liners, or bulbous plastic overlays here, just a sturdy, highly water-resistant boot with a retro, flat-lugged Vibram sole, traditional leather welt and liner, and full-grain leather upper. And while you might not want to strap any newfangled crampons to these beauties, they do just fine on mellow trails or kicking around town in true old-school style. $160; timberland.com