I wear letters pretty much on a daily basis. I am always promoting my sorority and I love to use my letters as a talking point.
I have letters on my car, on my key chain, on clothing that I wear, on water bottles and notebooks that I use at work. I always have letters somewhere near me.
There is no shame in wearing letters and it shouldn't matter how old you are. I know that I am still young (25) but I would LOVE to come across an elderly woman who is rocking it in a letter shirt (or something of the like) so I could engage in a conversation and even make a new friend!