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I'm not quite sure what else to call someone who wears a plaid shirt tucked into their jeans if they're not fat, retired, and over 50.
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Ummmm...
I've never posted a picture of myself with jeans, nor would I ever tuck in a shirt. Hell, I've only posted four pictures of myself on this site, two of which were only taken ten seconds apart. Besides, your description doesn't even classify as preppy.