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My first thought was Sex and The City! Love the fashion throughout the series and the movies. Each of the characters have different wardrobes and works great for different occasions.
When I was in high school the movie, "Clueless" came out and my girlfriends and I became clones of Cher.
Then in college it transitioned to Rachel's wardrobe from "Friends" (in the later seasons).
Now I'm more of a Charlotte from "Sex and the City" ~ I agree w/ the statement above, each character on that show having their own style and could work for different occasions.
Another good choice for me would be Vinnie's suits from "My Blue Heaven (1990)".
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