Artola's Jerry Boot

Artola, a small shoe company based in Brooklyn, designed a chukka for the bold. The "Jerry" boot has an extra eyelet and is available in loud colorways such as electric blue or eye-popping mustard. For more traditional dressers, there's a natural tan version that's bound to get some wear. Note that the shape of this chukka is more narrow than most. [Jerry boot, $175, nordstrom.com]