hahaha i was gonna answer this with just the hair item i wear a lot because at this point i don’t even notice my glasses as an extra item. my glasses in real life are the same as the round glasses in game so i wear those every day.
i also really like the headband item and wear it whenever one of them even remotely matches the outfit i wanna wear. it’s so cute ;~;
It’s not a 100% of the time kind of thing, but I have every color of ribbon and rubber toed sneakers. Most of the time my character wears whichever colors of those matches the rest of her outfit. It’s funny bc the character is supposed to be me, but is apparently into stereotypical girly things like giant ribbons and I am very much...not lol.
Rounded glasses and the black face mask. Haven't taken either off since I bought them, though my wardrobe has changed drastically through my time playing.
The crown has been my favorite headgear since New Leaf, that hasn't changed. Same goes for the Jester's Mask. Put them together, and you have some quality spook.