Generally speaking, the less detail something has, the more versatile it can be. Look for something with fewer design details.
Another thing to consider is the shape of the shoe itself and the thickness of the sole. Again, generally speaking, a sleeker last with a thinner sole will look dressier — where a clunkier last and thicker sole can appear more casual.
Here are two models I looked up utilizing the Herring site just because it was handy. The first one is a Church derby with a rounder toe and a thicker sole. The second is a sleeker Herring with a thin sole.
The lack of what could be deemed extraneous detail makes them easier to imagine in more situations.