Does a leather jacket work well with suede shoes?

OK, I'll bite. It can be good. imagine a rider jacket



and suede combat boots like these:



but it can be awful.

imagine the same jacket with, i don't know



but if it was a brown bomber, maybe those shoes would work. look at this picture:



both of those shoes are suede. it's not the materials that are the question, it's the styling/conventions/modes of dress.

If you are, what I will call "consistent", you should be OK. As ghdvfddzgzdzg describes, the DR looks good with more rugged shoes and the bomber is more versatile. I think the reason it looks particularly good on Willy is that he also has an OCBD shirt on, giving it a hair more formality, hence the "dressier" shoes. Desert boots would be another shoe choice that would probably work well.