The Rule: Match ‘Em
According to the tenets of man-law, thine belt shalt match thine shoes, and this violation is just the kind of thing that tends to get noticed. The black-black or brown-brown pairing is always appropriate and should be the default setting for any sensible getup. This is an attention-to-detail test, underpinned by a recognition that a dress belt isn’t really for holding up one’s pants, but for adding an element of connectivity to an ensemble. Keep the shades and patterns close, and keep that style reputation intact.
The Exception: Ribbons
Grosgrain or ribbon belts are a great way to dress down a suit, add a splash of color while tie-less, or simply let that inner prepster out to play for a bit. Have fun with the colors, and keep in mind that it’s not about matching so much as it is going. There’s also a great post at the Sartorialist on ribbon belts.
Never: Black & Brown
The point in breaking a rule is to show that unique personal style and a keen eye for details can elevate a man from well-dressed to stylish. Unfortunately, guilt by association trumps good intentions, and the black-brown mismatch is the belt crime most often committed by the under-informed. A conscious decision to join the ranks of the damned doesn’t make one the king of the tools; it just adds one more tool to the population.
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