You can’t go wrong with the classic chukka boot – British soldiers stationed in North Africa during WWII adopted this style of footwear in favor of their issued boots, and they quickly proliferated thereafter. It’s a timeless design that hasn’t lost its charm, making it a true footwear staple. If you’re looking to score a pair for yourself, now’s a great time: three pairs from some of our favorite bootmakers — Clarks, Frye and Allen Edmonds — are on sale for up to 50 percent off at 6PM right now.
Bushacre 2 by Clarks $100 $50
Jones Chukka by Frye $328 $164
Dundee 2.0 by Allen Edmonds $395 $238
