To the untrained eye, the Derby has “dress shoe” written all over it. But don’t let that basic thought process fool you into believing that these aren’t worthy of your next street-style photo-op. Throw these on with a pair of tapered or rolled-up pants and you’ll see what we mean. (The style is similar to oxford shoes except with an open-faced lacing system).

H by Hudson Hadstone Derby Shoes
Buy now for $160 at Amazon

Black Leather Derby Shoes
Buy now for $130 at Topman

Rockport Refinement Plain Toe
Buy now for $160 at Amazon