The 40 Most Stylish Moments in "The Simpsons"

Is Springfield the fashion capital of the world?

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Complex Original

Image via Complex Original

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Written by James Harris (Dr_TacoMD) and Chris Lewis (@cjameslewis)

In the tiny town of Springfield, there are a handful of budding fashion stars that would put any street style star or A$AP crew member to shame. With more than 500 episodes in 24 seasons, Homer, Bart, and the rest of Springfield's finest fashionistos have had their fair share of stylish moments while navigating the wacky adventures that come up every day. 

The Simpson family and the folks they live with are supposed to be a parodied mirror of typical, average Americans. So while the majority of their time is spent in clothes that don't spark the imagination, they all have days and moments when their style gets turnt up. Since 1987, when the show launched, these are The 40 Most Stylish Moments in The Simpsons.

RELATED: The 50 Best Simpsons Episodes

40. Daredevil Bart

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39. Springfield's Most Stylish Criminal

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38. Barney Gumble's NASA Jumpsuit

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37. Poochie's Rad Style

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36. Homer vs. Rex Banner

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35. Tomacco Farmer Homer

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34. Bart's Utility Belt Trumps Jimbo's Cord

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33. Counterfeit Blue Jeans

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32. Colonel Homer

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31. Moe's Dating Outift

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30. Homer Goes Grunge

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29. Homer, Ad Exec

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28. Flaming Moe's

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27. Homer's Patriotic Outfit

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26. The Party Posse

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25. Homer Simpson, Hipster

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24. Bart's "Down with Homework" T-Shirt

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23. Kirk Van Houten's Musical Debut

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22. Bart Simpson, Mafioso

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21. The Be Sharps

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20. Stonecutters Homer

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19. Milhouse's Flood Pants

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18. Senator Homer Simpson Fantasy

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17. Homer's Concert-Goin' Jacket

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16. Grampa's Sharp Salesman Suit

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15. Mr. Burns' Driving Outift

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14. Abe Simpson at Woodstock

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13. Bart's Hipster Glasses

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12. Homer and Marge's Prom Ensemble

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11. The Knoxville Wig Emporium

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10. Homer's Leather Jacket With Tweed Patches

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9. Krusty Goes Alt Comic

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8. Bart and Hugh Hefner

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7. Mr. Burns Dresses as Jimbo

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6. Bart's Striped Suit

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5. Assassins

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4. Young Skinner

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3. Mr. Burns' Gorilla Vest

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2. Homer's Muumuu

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1. Homer's Pink Shirt

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