WHAT DID HE MEAN BY “this season IT item” like bro is breaking the fourth wall

Haha no, it means in fashion. Like in "those shoes are SO LAST SEASON" meaning the shoes are not popular now

The earrings being "this season's 'it' item," just means they are the most popular fashion item during the current season. As in everyone is buying them, so it was pretty easy for Lorenzo to find a pair.

great i made myself look like a fool. thanks for explaining it to me bc idk what the helly i was thinking