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Ama Shigure in always wears some kind of cat-eared cap, to the point where Rin wonders if he's ever seen her without one. SHUFFLE! It hides her ears.
Ace Attorney In the fourth game, Phoenix Wright gets one. It looks just like a ski cap, and it has a hidden camera.
In later games, Ema Skye gets a cute, pink hat to go with her glasses.
Angel Starr has a bento-themed hat. Picture 1 ◊, Picture 2 ◊.
Trucy has a top hat to go with her magician style.
Ini Miney wears a beret that gets abused during the course of the case.
Olga Orly normally wears a red and white bandanna, but when going undercover as a waitress in a Russian-theme restaurant, she wore a fur hat in the typical Russian style.
Jake Marshall has one, as part of his literal Cowboy Cop clothes.
Gregory Edgeworth gets one in Gyakuten Kenji 2.
CLANNAD: Ushio ( Tomoya's daughter) has two hats, a nice sunhat and a school/sailor hat ◊.
Hanako's black flatcap ◊ from .
Katawa Shoujo A number of the women from have nice hats, such as the previous Beatrice, Umineko no Naku Koro ni Eva Beatrice and Lambdadelta.
Kud from has Little Busters! a wide, white hat decorated with a button and two little ribbon strands to look vaguely like little wings ◊. It's so important to her image, in fact, that the interface screen for her spin-off game Kud Wafter is decorated with buttons, along with dog paws and gears.
Ojou in absolutely refuses to remove her nice hat. It's black and has two bells hanging on it. It doesn't even come off when she's bathing or swimming. The closest to removal it gets is Hiroshi putting a 'second hat' (read: Archimedes) on top of her head.
Suika Maino Honma from wears a sailor-esque one, complete with Yumina The Ethereal Sailor Fuku.