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The 40 Most Stylish Moments in "The Simpsons"

25. Homer Simpson, Hipster

"The Day The Earth Stood Cool"
Season 24, Episode 7

Homer is a middle-class white guy who loves cheap beer, slacking off, and going on wacky adventures. In other words, it only took a few fashion transformations for him to become a full-fledged hipster. By adopting the latest insufferable style trends, Homer joins the ranks of cool kids who have flocked to Springfield, which, of course, makes it played out and not cool. It's a vicious cycle.

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