Timberland Men’s Earthkeepers City Chukka boots, $150
The brown/black coloring of these boots makes them easy to pull of with dress pants, khakis and jeans. Plus the sneaker-like bottom makes them comfortable and keeps you from slipping in winter weather hazards while the inside lining is made to wick away moisture. However, for anything more than a light snow or rain, you may want to get them waterproofed.
Available at Timberland.com and in most department stores.
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