The moment a man isn't well-dressed, is when his clothes aren't appropriate for the situation. If you're dressed up like Bill Laimbeer or a real-life Roy Rogers; it's rare that you're in-tune with how everyone else is dressed. You shouldn't dress exactly like everyone else, especially if they're wearing square-toed shoes and polo shirts, but think about the context in which you're engaged. If at any time you have to ask yourself if something will fly, the answer is always no.
It's not appropriate for every situation.