Our newest release's old history.

The Finer Details.

By definition, Chukka boots are ankle-high with only a couple of eyelets. From there, we take our own direction designing our boots in a manner we believe will be enjoyed the most. Our final decision? Three eyelets as well as options for both full-grain Italian calfskin upper and water-repellent suede. To deliver comfort unseen in Chukkas before, we use our exlusive Memory Foam for that extra edge. 

Rise of their popularity

Rumor has it that polo players ignited this trend with their off duty styles. Beginning in India, British army units brought this trend thousands of miles to the West. What directed this style from being a matchstick to a wildfire? The Duke of Windsor first wore them in the States back in 1924. Almost 100 years later and we are still chasing his style. Although, this was not always the case. At first, the Chukka design caused tension through living in between trends. Were they meant to be dressy? Or belong in the casual genre? This difference of opinions is where they were meant to reside and have thrived there ever since. 

Trademarked for Comfort.

Chukka’s popularity arose from occupying a distinctive state between comfort and style. They proved more comfortable than the formal as well as casual boots that were common back then, bewildering everyone's preconceived idea of boots. Now the question arises- if these shoes' original intent was comfort, then how can we bring these to the next level? The answer was easy. W&S Chukkas joined our Crossover fleet to provide maximum comfort within the casual boot. The high-traction, thermal rubber outsole touches on its lineage of durable rubber soles. 

Chukka Boots Now.

As we prepare ourselves mentally and physically for fall, these boots migrate to the front of our closets. Common on the downtown streets of New York and other major cities, we’re looking forward to hitting the ground running with our newest style. We often see the boots paired with casual jeans and neutral colored chinos. For the cooler days to come, throwing a weathered leather jacket will top off the look. 

Check out our new Crossover Chukkas to keep up with the latest trend.