@Ebonysdagger  
I can say with certainty that one of those hats belongs to Megumin (Konosuba)

Had to look for ten minutes until I found Rin, well played.. well played.

Kukuri from Mahoujin Guru Guru, you’ve forgotten

@Ebonysdagger  
Yes Hermione is there on the bottom right with brown hair and black cloak

@Ebonysdagger  
by crazy i mean “crazy awesome”

@RIG  
Lina isn’t crazy. Naga the White Serpent is crazy. Lina is just a bit too powerful for any bandit’s good… and unfortunately knows a spell to summon the Lord of Nightmares which means she could accidentally unmake her entire universe.

Is that the fucking crazy bitch from slayers?

@Ebonysdagger  
+1

And unless I’m missing my guess another four I know of implied by those witch hats that have no one wearing them.

Hm… lets see here. Kiki (Kiki’s Delivery Service), Louise (Zero no Tsukaima), Uma (Magical Pokaan), Lina Inverse (Slayers), Atsuki Kagari (Little Witch Academia), Patchouli Knowledge (Touhou), Konata Izumi (Lucky Star), Twilight Sparkle (MLP:FIM), Star (Star vs The Forces of Evil), Tanaka Punie (Dai Mahou Touge), Izetta (Izetta: The Last Witch), Maria (Maria the Virgin Witch), Bayonetta (Bayonetta), Zatanna Zatara (DC Comics), Scarlet Witch (Marvel Comics), Tohsaka Rin (Fate/Stay Night), Yuko Ichihara (xxxHolic), Mismagius (Pokemon), Yoshika Miyafuji (Strike Witches) to name the ones I know specifically. I think Hermione is in there but I’m not a fan of Harry Potter so I’m not certain.