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I only graduated in 2010 so I still have a few t-shirts that I wear when I'm running errands, working out or just having a lazy, hanging around kind of day. I'm sure those will eventually become worn out and unwearable. When they do, I'll probably buy a new letter tee, just to make sure I have one on hand should the occasion arise to wear it. (Hmmm...maybe I'll buy one now...heading to a Greek clothing website after this....) I'll wear my lavalier to sorority functions, same with my hoodie.
I don't think there's anything wrong with wearing letters as an alum; I think the thing is you just have to understand that there are going to be people who were not involved with Greek life may think it's odd.
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