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I think in some cases it is because people are being forced to dress in a way that is not their personality. It's hard to be creative when you are only wearing things because people tell you that you are supposed to. Not sure if that makes sense to anyone or not.
For example, if I have never worn a suit before, but suddenly find that I am required to wear one, I would do it, but would not know how to tie a tie, would probably use a clip-on, would not even know about the different types of dress shirts and cuff-link options, etc.
Yes, some people just know how to dress sharp, no matter what they are wearing, and some people know how to dress sharp when it is something that they enjoy wearing, and some people just don't care about dressing sharp at all.
Personally, I wear cargo shorts, sandals and short sleeve shirts 99% of the time now. I don't see any point in wearing anything else.
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