I will start and I know TNT will be on this like mad. I wear a belt that has a match to the shoe in some way. I have a white belt, and wear it sometimes with a white shoe. But I also wear a navy belt, a red belt, or a grey belt with a white shoe, so long as that color is also in the shoe. Same thing with black shoes, where I might wear the purple belt with a black/purple shoe.
Here's the key. First off, you need to have rationale behind the color choices and there needs to be color cohesiveness. I don't live by the shoe/hat/belt rule, but I do live by the shoes/belt rule 100%. Look, a sense of style and personalization is important. Whatever you do, you have to OWN it. You absolutely need to be comfortable and confident with what you have one, and live by the "Look good, play good" motto.
And IMO, Marty Hackel is a "hack."