This is a spinoff from the Vince Young talk in the JFF thread. This one about Iverson is the best I've heard: http://larrybrownsports.com/basketball/allen-iverson-bought-new-clothes-on-road-trips/118752 Just wow.
I have to admit, I've been tempted to do that. But mostly with just socks. Those things are a pain in the ass to match, fold and put away once a week.
It would be highly liberating -- and fairly cost efficient, honestly -- for me to just toss all my socks and buy new ones. I don't know why I haven't done it. I should also put a ten year max on all t-shirts worn as undershirts.