With these updated styles, your biggest problem won't be figuring out how to wear them—it'll be deciding which gorgeous pair to choose.
An unexpected color like mossy green will bring out a new dimension in a navy suit.
Fratelli Rossetti ($690)
The Chelsea boot pairs perfectly with tapered trousers.
Banana Republic ($158)
Worn with a black suit, a black suede captoe delivers a tonal match that will add some texture to your outfit.
The black single-monk is the sleekest, most sophisticated, most versatile shoe around.
For a bit of Euro flair, wear a tasseled loafer with pants that graze the middle of your ankle.
A dark-oxblood shoe is a beautiful complement to a charcoal-gray suit.
John Lobb ($1,640)
Brogue boots add the perfect rugged touch to your favorite casual suit.
Allen Edmonds ($375)