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The 40 Most Stylish Moments in "The Simpsons"

5. Assassins

"Bart's Dog Gets an F"
Season 2, Episode 16

NEd Flanders is the first person in Springfield to take part in the latest workout craze by purchasing Assassins. The shoes come complete with velcro straps, a water pump in the tongue, a built-in pedometer, reflective sidewalls, and little vanity license plates (MSRP: $125). Homer of course has to have a pair, as does A$AP Rocky, who copped a pair of Raf Simons 2008 boots for a whopping $1,800. If only Santa's Little Helper hadn't chewed up Homer's pair...

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