Some age old questions will never be answered. But *that other* age old question, whether your shoes and belt have to match, are going to be answered right here and now. Aaron Marino of alpha m. says that matching shoes and belt pulls the look together and knocks your outfit out of the style park.
You don’t look *silly* if you don’t match your leather but there is a degree of style IQ that is required if you are not going to match your shoes and belt. The way that Alpha sees it: the more dressy the outfit, the more the necessity that shoes and belt should match. If you are are wearing a suit, your belt and shoes should match in color AND leather finish & texture (ie: shine, finish). Dress shoes require a dress belt (buckle shiner, less thick).
Brown is a different animal altogether. Alpha gives examples. Matching browns is tough. You should NEVER match brown by memory as it never works. Save yourself time and gas money, wear or take the shoes with you when you buy the belt. Tip: many dress belts are reversible. Another consideration is whether you will actually find a belt that matches. Shoes have a bunch of brown tones. So you don’t have to match exactly but it has to be close. The good news is that the pant breaks up the slight differences in shades (get it as close as possible).
Ultimately, it comes down to the shoes that you are wearing rather than the outfit. If you are wearing dress shoes, the belt should match. If the shoes are casual, the belt that you chose should coordinate rather than match. With coordination, take in account the outfit. Experiment because there are no rigid standards with casual shoes. The only rule is not to wear a dress belt with casual shoes. Alpha covers examples of coordinating shoes and belts.
Belts and shoes– they should match in some situations like with dress shoes or a business outfit like a suit. If you have chinos or jeans, you have more flexibility. If you are wearing casual shoes, the sky is the limit. It just have to coordinate with the outfit.