I have a system.
It used to be that my shirts were piled in a big...pile. And each morning, I'd grab one and put it on. I'd grab one of my favourites. I'd end up wearing four or five shirts in a single week, with little variance from week to week. I had about twenty-thirty shirts, but the lame ones were kept at the bottom of the pile so I didn't have to sort through them.
But, my borther then gave me some of his shirts that he didn't wear.
So I made a useful system: [i]two[/i] piles of shirts. I'd take the one on the top of the first pile, wear it, and when I got shirts back from the laundry, I'd put it on the second pile. Once the firt pile was gone, I'd flip the second pile back onto where it was and start over. Thst way, I wore each shirt once. Wouldn't wear the same shirt more than once over the course of a month.
But! Now because some shirts are quite lame and some are fab and such, and the first pile spreads out so much, I will pick and choose a bit, and occationally I'll completely skip the worst few.
These are my short-sleeved button shirts. The thing I wear 300+ days of the year. My long-sleeved button shirts are in my dresser.