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I remember when I was young, seeing photos of my Mom in the 80's and being horrified - both at how uncool she dressed, but more importantly, how she didn't know it was going to be uncool. I couldn't comprehend how everyone just wore such embarrassing things and then-
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But lately, after having spent time around people who are 'into' fashion, I've really come to appreciate trendy, novel clothing. I've slowly realized that the point is not to have timeless pieces that don't embarrass you later, the point is to demonstrate-
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cultural savviness by being able to pick up on things on the "front lines" of style - it's a form of risk taking that signals competence, wealth, confidence, and artistic ability. It's a lot closer to a game than I realized. Now I do some trends without feeling gross about it!