I still wear my lettered hoodie all the time and occasionally wear lettered t-shirts. And ZTAngel is right, you see a lot of "vintage" party shirts out and about - saw a Chi-O bid day shirt from 1999 in my real estate class a few months ago, for example. My boyfriend just bought me a lavalier since I had given mine away to my second little and it's kind of a family tradtion in my chapter to not wear lavaliers after graduation so we're thinking I'll attach it to my Tiffany's bracelet instead
Still have the small gold/black letters on my car just because I think it's neat to see others as well. I agree a little bit that it looks odd to see an older woman in letters but Greek Life is big down here in the South and if I saw an older woman in letters out and about I would assume she was just really involved in alumnae stuff, and that's a good thing
I feel like there's this taboo about wearing stuff like that as an alumni but I do it anyway because I'm proud to be a member of my org!