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It depends on your job and what you are trying to accomplish. I enjoy dressing like a slob sometimes, but if I need to go out on a date, I can turn it around and look like an entirely different person! I love my clothes. I love to look nice when I go out. Can't have enough clothes and shoes in my opinion!!!
Dressing well can help advance someone into upper management, but if one overspends on designer clothes, I can also see it backfiring and being seen as a fashion victim or spendthrift.
Also, if one takes good care of their high fashion designer goods, they have better resale value than regular clothing and accessories.
'Key pieces' (like simple blazers or slacks) can have some sort of return but if you buy something that is TOO trendy, it probably won't last through the next season. (Like gouchos- cute but no one's wearing them anymore)! In that case, you probably just wasted your money. But if you had fun with it will it lasted then I guess it was worth it.
I think the best ROI on clothes is the way they make you feel. There is nothing like wearing an outfit that makes you feel like a million bucks. Maybe some pieces will turn into great, rare vintage and then have a monetary ROI.
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