Trivia: The scene where Macaulay Culkin was waiting at the door for the babysitter and imagined the three burglars was the scene that inspired the box-office hit, Home Alone. (01:16:10)
Trivia: In the scene in Maizy's class near the beginning of the film, the little girl with long blonde hair sitting at the desk next to Maizy is a young Anna Chlumsky, who went on to be the star of 'My Girl' and 'My Girl 2'.
Chosen answer: He's being sarcastic, as Buck says in the beginning some of his hats anger a lot of people, which probably connects to when his hat gets taken by one of the teenagers at the party.
Buck is actually referring to his aviator style hat in the earlier scene about people being angered by it. He's wearing the fedora style hat in the scene en route to the party. But I agree the guy was being sarcastic about teenagers.
The black purse bedside to the possible 'pile of bunched-up blankets' looks like Chanice's from later scenes; suggesting the writers or Hughes changed the script after the bedroom scene was shot to Buck's simpler but delightfully funny half-conversation with her on the phone.