When should I wear an anime cat ear hat in public?

Ok, it's actually a fox ear hat, but I know cat ears are more popular, and are easier to picture. They look like that but are in orange with black tips. The front of the hat is covered in 26 different buttons from Hetalia, My Little Pony, League of Legends, Assassin's Creed, Minecraft, and Fullmetal Alchemist. It looks cute on me, but I'm worried I'll be teased for wearing it in public. I already wear geeky graphic tees often, and I have a Rainbow Dash school bag. It is light blue, has wings on it, and a little felt rainbow tail at the bottom, along with a Rainbow Dash on the front pocket. I've only had one person say "Really?" when they saw it, while most people have complimented me on it. I have also been teased in the past for wearing a wig to school before, which was a bad idea. Should I take the risk of wearing my hat in public? (I'm in high school by the way) If you're not a nerd, would you think it's weird to see someone wearing a hat like this?