Demystifying Dress Shoes

There are many different kinds of dress shoes with different fashion “rules” and implications. When most of a dress up we just chose what we like and go from there. Sometimes people seek more and wish to learn the rules of fashion. We’ve compiled this handy guide here to help you get started.


  • The dressiest oxford men’s footwear selection. Sleek, refined, most often sold in black or brown. 
  • Style variations include plain toe, cap toe, brogue, and whole cut. 
  • Appropriate for a suit, if casually styled works sport jackets or odd trousers. Do not combine with jeans. 




  • Less dressy than balmoral oxfords identified by lacing system sewn outside of shoe.
  • Can be worn with a suit but more versatile with different styles of dress. Can be worn with jeans assuming they are casually styled. 
  • Style variations include cap toe, wingtip, brogue, wide variations in materials such as suede and leathers.   




  • Are meant to be worn when the weather dictates protecting the ankles from water, mud, and snow – in levels of formality they should not be worn with a suit although they can if the weather calls for it. 
  • Variations include cap toe, broguei, wingtip, wide variation in materials.
  • Appropriate with sport jackets, odd trousers, or jeans. 
  • Boots should be considered only if local weather warrants a pair.


Loafers (Slip-On)


  • The least dressy choice, they are a product of comfort and convenience.
  • Meant for lounging and  for dressy occasions. Go well with jeans and chinos.
  • Wide style variations. Common variations are monk straps, penny loafers, and unlaced moccasins.
  • A travelers best friend