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I'm 27 and I wouldn't wear letters out unless it was mandated by an alum event or something.
It's not that I'm not 'proud' or anything, but just like other articles of clothing that I wore in high school or college, I just feel I've outgrown them and tend to prefer to dress more my age. I still do have my shirts and stuff, but they are tucked away in a drawer. Some people put them on a quilt too.
I don't regularly wear t-shirts anymore either unless it's to sleep in, so that might be another reason why the lettered shirts don't ever make it out.
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