I have an entire collection of T Shirts from places I've never been and things I haven't done. They are all thrift store finds and some have led to interesting conversations. I started buying them (and still do) if I like the designs. It's really surprising how many people actually read the shirts I wear and I'm frequently stopped and asked about what I'm wearing. Sometimes it's awkward....but that's kind of my thing. It's a running joke in my house that I never go anywhere but I have T shirts from everywhere. You've reminded me that it's time to refresh my collection! The best conversation bait is a shirt from a neighboring city - Buffalo shirts worn in Rochester are an especially good way to attract a conversation. I don't do political shirts - only landmarks or local events - and they have to be for events of places I look like I might actually have visited/attended. Restaurants, BBQ, bars are an easy sell for me. Fun runs, marathons, etc - not so much.