My tennis shoes are a 2 year old pair of Nikes, but my other "main" shoe is a relatively expensive pair (still under $100, but over my normal $40 threshold). The tennis shoes are black, the Merrell's are tan, and my heels are black.
When I worked it was business casual, so I would wear the heels if I dressed up and switch between the tennies and the others if just wore khakis.
I have narrow feet with really high arches, so it's difficult for me to find shoes that I like. What I need to do is buy multiples of a pair that I like in every color they come in because I'm so picky.