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.
Rule #45
An unexpected color like mossy green will bring out a new dimension in a navy suit.
Fratelli Rossetti ($690)
Rule #46
The Chelsea boot pairs perfectly with tapered trousers.
Banana Republic ($158)
Rule #47
Worn with a black suit, a black suede captoe delivers a tonal match that will add some texture to your outfit.
O'Keefe ($545)
Rule #48
The black single-monk is the sleekest, most sophisticated, most versatile shoe around.
Church's ($610)
Rule #49
For a bit of Euro flair, wear a tasseled loafer with pants that graze the middle of your ankle.
Tod's ($625)
Rule #50
A dark-oxblood shoe is a beautiful complement to a charcoal-gray suit.
John Lobb ($1,640)
Rule #51
Brogue boots add the perfect rugged touch to your favorite casual suit.
Allen Edmonds ($375)












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