Well, it doesn't matter for Casey if he wears ugly suits cuz he could get offered a job even if he quit coaching with us. That's the way it is. Same goes for Pops, Van gundy, and Thibs.
As for us regular people, we have to dress nice to impress our potential employers, co-workers and all. But once you get 'respect' in the workplace, then that's probably the time you can wear a Van Gundy-esque fashion style.