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I think this is too open-ended of a question. To answer it we'd have to define what "fashion" entails and what "dress well" means. Personally I think "dressing well" is very subjective. Girls at my school think they dress well but I think they look ridiculous.
I think it's very possible for people to look good without being "in the know" with designers and collections and latest trends, etc. Tom Verlaine said that "true style is incidental." I really think that's true (to a certain degree) because looking good is not all about putting together pieces like you see in a magazine...
It can also be the other way around, where people really understand fashion and have an eye for what looks good, but don't really know about/feel like dressing well themselves well.
All in all, fashion and dressing is not about "knowing" I think... Fashion week is right now and I have no idea what the Oscar de la Renta collection looks like. I don't really care about glamorous beautiful gowns. I see fashion as sort of a canvas for creativity. I love it when designers make stuff that at first sight make you go "what were they THINKING!?!?!" but then the more you look at it, the more you realize that what they created is actually beautiful. You only didn't realize that it was beautiful right away because it's not what society touts as "beautiful." And ok i'm going off topic now.
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