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We live in a time when we no longer need to be tied to a desk, punching buttons until we punch out. Cords have been cut, and we’re free to carve a path wherever we go. But for that kind of spontaneity, you need a style that can adapt to different situations. For a look that can carry you through a morning in the city and an afternoon in the great outdoors, turn to Timberland. Here we’ve paired Timberland Boot Company’s Lineman Boots, which were inspired by the rugged boots lineman wore in the early 1900s while climbing poles and lines, with a denim, slim fit Mumford River Shirt and Timberland’s Thompson Lake Slim Fit Cargo Pants. For the cold months ahead, we added the Mount Webster Leather Bomber Jacket, which is ready for the strong city winds and the chill of the great outdoors. We’ve also included some reading material to toss in your Adkins Leather Duffle Bag for when you have to hit the subway. No matter where the day takes you, you’ll be ready.

  • Timberland Boot Company 6-inch Lineman Boots – $475
  • Timberland Mumford River Slim Fit Denim Shirt – $98
  • Timberland Thompson Lake Slim Fit Cargo Pant – $78
  • Timberland Mount Webster Leather Bomber Jacket – $648
  • Timberland Adkins Leather Duffle Bag – $348
  • Timberland Bartlett Multifunctional Wristwatch – $179
  • Freeman’s: Arrival$12

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Unzip your coat and have some mulled wine on the house—you’ve arrived at your final gifting destination: The Holiday Gift Guide. It’s like your friendly neighborhood one-stop holiday shop, except instead of balsa wood ornaments, ours is packed with thoughtful gifts for everyone on your list. Future heirlooms, small-but-significant stocking stuffers, and gear for getting out there (or staying in)—are all right here. There’s no music playing in the background though, so you’ll just have to hum Bing Crosby while you click around instead.

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