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Timberland Earthkeepers Chukka Boot

In general, Chukkas are a suitable middle ground between thick-sole boots and lightweight sneakers. This pair by the good people at Timberland uses a washed cotton canvas upper to make your foot feel weightless, but still constructed with the ruggedness to fit in next to your go-to pair of wheat-colored 6-Inch Premium boots. The heel tab on these makes it easier to get them on and off your foot, if you actually even feel like taking it out of the cushioned footbed.

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