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I wear flip flops, shorts, and a ball cap nearly every day in the summer that I'm not working. I dress for success at work, but when I'm off, I don't give two ****s what anyone thinks of my clothes. I dress for my comfort not your preconceived notions.
I've met some guys that you would consider to dress like slobs, who could buy you several times over without blinking an eye.
Sorry, never judge someone based on what they wear or drive. Some people don't give a crap about what others think of them, usually its because they are sitting on a fat bank account and are fine with life on their terms. I'd rather deal with a rich guy in shorts, than a wannabe rich guy in a cheap suit...
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