If you’re looking for a dress shoe that can easily cross back and forth between the territories of formal and casual, pick up a pair of derby shoes. And if you want a comfortable pair that won’t fall apart after heavy wear, these by Beckett Simonon are set on durable SBR rubber soles that provide plenty of support and traction. Plus, the Vachetta leather lining manages temperature, absorbs sweat and controls odors.

$239 by Beckett Simonon