They say, “rules are meant to be broken.” We say “sometimes.”

So what of that rule about only wearing black shoes in the evening? “No brown after 6pm” is pretty ridiculous; there’s no reason you can’t pull of brown shoes in the evening. All you need to consider is this:

 1. Where are you going?

If the answer is “the opera,” don’t wear brown. Take into account the formality of the event you’ll be attending. If you’re getting dinner with the CEO of your company at a swanky restaurant and you’re wearing your nicest suit, you need a formal pair of black shoes to go with the occasion. If it’s more of a relaxed situation, you can pull off browns shoes with, say, a navy suit. Stick with a dark brown because you also need to ask yourself…

 2. What time is it?

Forget hours and think about the light. You want to keep your lighter colors in the daylight while you match the night when the sun goes down. Dark brown shoes are less jarring and look better with night attire.

 3. What’s the season?

It kind of goes hand in hand with measuring the time by light; if it’s summer and the days are long you’re going to see more light colors come out later and later. If you go to an event that starts at 4 or 5, no one expects you to go home and change just because it gets dark at 8—that’s no fun. But if it’s winter, a very formal event, and you’re arriving when the sun’s going down choose black shoes to be safe.