I actually saw a conversation a few years back on this very site where somebody that wears these flat brimmed hats (not elmo or sesame street just the type of hat) said that he only wears them ironically, and he just said that like everyone knew what it meant and just moved on to whatever else he was saying.
And then someone else calls him out on it and says "hold up, what the hell does it mean to wear something ironically, how I'd that even possible"
Basically the guy explains that he actually thinks they look stupid, but because he's wearing it with the knowledge that it looks stupid, it's actually very cool and stylish
I've been using the search function again and again to find that comment it was so weird