10. Homer's Leather Jacket With Tweed Patches
"Secrets of a Succesful Marriage"
Season 5, Episode 22
As the distinguished professor of a class that teaches the secrets to a successful marriage, Homer knows that he needs to wear the sartorial uniform of a learned man. Rather than conforming to professorial norms, Homer reverses the formula by putting tweed patches on a leather jakcet. Don't be surprised if your prof starts rocking this look, since Homer is a certified #influencer.