Timberland Brook Park Chukka Boot

via timberland.com

This is one of those cases where a Tim looks more like a Cole. These Chukkas from Timberland are more office appropriate boots compared to their iconic brethren, and don't scream its namesake with a large tree stamp on the outer heal, making them our top pick for this price point. While Timberland does offer another chukka with nicer leather, they tend to fall apart sooner than one would expect. These however, offer longevity, at lower risk (cost) and keep mother earth in mind as the inner lining is made from 50% recycled plastic. Note on wear: make sure you wear high socks with these as the tops can feel mildly sharp against your ankle bone if you go with no shows.

Available on timberland.com for $130 

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