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The Eastland Jack is a plain leather chukka boot with a lace-up front, a foam insole and a rubber-and-EVA outsole. It is a casual everyday boot rather than a weatherproof one, since it has no Gore-Tex lining. The best new price is $87.50 at Macy's as of November 7, 2026, with 7 stores listing it new.
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Lowest price we've seen: $39.35 on Nov 7 at Zaffy. Tracked across 14 stores since Nov 7.
Rated 4 out of 5 from 115 ratings, the Jack is generally well received as a comfortable, good-looking casual boot. Complaints tend to focus on the light sole and lack of weather protection.
Eastland brings you these practical unisex chukka boots for men. The outsole on this particular boot has been made from EVA.
