This is so off base. I'm a 40 something professional who is very successful, drives a very nice car, owns a home and already has my 14 year olds college paid for and I work in a backwards hat and workout pants every day. I usually sport a 2 foot long beard and currently have a mo-hawk. I am looked at as a leader in a fortune 5 company because I'm good at what I do. No one care how you look anymore and this line of thinking is primitive.
One of the richest people on the world agrees.
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And if I'm reading between the lines of where you want him to shop, it almost sounds like you want him to dress like a....nevermind, I'm not going there.