"North by North Quahog"
Season 4, Episode 1

Usually, Herbert the Pervert is rocking a cozyboy robe and walker—a uniform we can't wait to rock 60 years from now. However, Herbert knows that, when in Rome/an 8th grade dance, do as the locals do. So he shows up in a dope snapback, a super sick bomber, and perfectly cuffed denim that sit above immaculate cap-toed kicks. We're not sure if the youth at the dance listened to his advice to "stretch out those creamy hamstrings," but he may have won best-dressed for the night.