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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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OLIVERS Passage Pants are obsessively engineered and built with a lightweight 4-way stretch fabric, durable materials and a streamlined design. The combination of comfort, stretch, durability and performance makes them as dependable as a pair of jeans and as comfy as a pair of sweats. Whether you’re wearing them at the office, on a weekend adventure or around the house, these pants are made for the man on the move. Ditch the denim and discover the wonder that is the OLIVERS Passage Pant.