Matching Rule #1 – Match The Leather Colors.

This rule couldn't be simpler. Lucky you! In general, the more contrast there is between your belt strap and your shoes (or even briefcase or messenger bag), the less stylish you're going to look.

If you've got a dark brown belt strap, the most logical choice for shoes would be dark brown ones. If your shoes have a distinct oxblood color, then an oxblood belt strap is the way to go.

Nevertheless, don't worry too much about a slight difference in the tones of both items. It's not a big deal if, for example, your dress shoes are darker in the front than at the back. As long as they're closely similar in color, you got the job done.

Matching Rule #2 – Match The Metals.

Essentially the same concept as above. You want the belt buckle to have a very similar color to the metal on your shoes if they have metal. Specifically, we are talking about the buckles on monk strap shoes.

Gold goes with gold, silver with silver, etc. You might even want to take it a step further by matching these buckles to the metal in your other jewelry, in particular your watch or whatever rings you're wearing.

A notable exception: your wedding ring, which it's perfectly acceptable to keep on at all times.

Don't let matching make you discard sentimental or irreplaceable items, such as your wedding ring or an heirloom watch. Again, the real priority here is matching the leathers, as mentioned in rule #1.