"The Last Temptation of Homer"
Season 5, Episode 12
In 1993, Bart's thick-rimmed glasses cast him into nerdom. Turns out, he was 20 years ahead of his time, pre-dating Kevin Durant, Russell Westbrook, and mad hipsters. This stylish look wasn't appreciated at the time, but as we continue to be influenced by the '90s, it only becomes more and more clear that we should all take style tips from Springfield.