Welcome to the kilted rabble.

No, there are no silly questions. But it may at times be silly not to ask

There will undoubtedly soon be people chiming in to say that leathers ought to be the same colour...

On the other hand, it will depend a little on what nuances of e.g brown we are talking about. I generallt go for leathers of the same colours, but I do have a pair of hiking boots (used casually) that are so dark brown that it is difficult to notice a discreppancy in colour.

There is also something I like to think of the "feel-good-factor", meaning if you feel good about something it is right for you.