I collect button down denim shirts. Business and event shirts are fun. My NRA, Browning and S&W shirts are favorites with the libs.
I'm partial to various micro-brewery shirts. I even have a matching Redhook shirt and tie. Matching up ties is always fun. I haven't figured out what tie to use with the Tupperware shirt. I usually pick the Spam or Pillsbury Doughboy shirts.
Comdex shirts go with the Dilbert tie.
On test days, I either wear Einstein or the Thinker.
Harley ties go well with Daytona or Sturgis bike week shirts.
My Patriots shirt got into the mix last week.
If you're ever down in Tempe, look them up. Even a transfer through Phoenix, they're relatively close to the airport (prolly $30 round trip via taxi, but it's worth it to skip the airplane food and get a sample of their work--they sell great beer in 'growler' size jugs).