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The Timberland Classic Boat 7-Eye Leather Chukka Shoe will match your water outfit whether you're wearing board shorts or a full yacht tuxedo. The hand-stitched premium leather upper has the traditional look of a boat shoe with a bit more support and style around the ankle, while the siped rubber outsole provides maximum traction on everything from the deck to the cruise-boat dance floor.

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Probably dumb because it is made as a boat...

Probably dumb because it is made as a boat shoe, but I am looking for something stylish for the snow. This bad boy waterproof/water resistant


Obviously, leather shoes are going to absorb water to some degree. That being said, you can combat this by using a quality leather treatment combined with some water proofing. Here is some stuff that BC sells:

I recently purchased Kiwi Heavy Duty Water Repellent for my leather hunting boots and it seems to work great so far.