Chukkas are ankle high boots with two to three eyelids for lacing. The name for this shoe comes from the game of polo and was popular in the 1940s and 1950s. Chukkas are interesting because all shoe makers have taken on this style from dress shoe experts like Cole Haan to Nike. Clae has come up with the Strayhorn, a nice mix of dress and casual. This athletic wool chukka is not for all climates and may have your feet warmer than needed. The navy speckled look is a rare change from your standard leather chukkas.

Price: $120
Source: Clae