As consumer journalist Rob Walker reports in his book Buying In, "the legend goes that the first 'urban' buyers of Timberland boots were New York drug dealers - guys who had to stand on the street all night and needed the best possible footwear to keep them warm and dry."

Can they be worn in the snow? Because Timberland's outdoor and working boots are waterproof, insulated, breathable, and have great grip and comfort, they are perfect for snowy conditions. They will provide grip in deep snow and traction in slush and icy water, while also keeping the feet warm and dry.

The culmination of the Swartz family's journey came in 2011 when Jeffrey Swartz, Sidney's son, and Nathan's grandson, sold Timberland to VF Corporation. The story of Timberland is indeed a testament to the vision of three generations of the Swartz family.

Yes, you definitely can wear hiking boots every day. All Timberland boots offer optimal support and premium leather uppers for lasting durability. As with any shoes, it will also take less time to break in hiking boots if you wear them often as you hike the backcountry on your next backpacking trip in cold weather.