I don't wear my class ring very often, but I've worn it a few times since high school. I think it depends tho, because some people wore their class ring like a regular ring and didn't make a big deal of it, so it doesn't seem out of place for some people. A Varsity jacket, in my opinion should be retired after college for the most part. It's cool to wear it every now and then, but you should be wearing something that isn't your high school jacket out to bars and such.
My two thumb rings I've had on since I was a freshman in high school, and my favorite pair of jeans I got when I was in high school. They're about ready to be retired tho. Granted I'm in my early 20's, but still.