I just found a headgear combination that looks absolutely amazing. For those that have the PC version, (or the Falmer Crown on PC version), equip the Falmer Crown with the Jagged Crown. They both equip, and they look AMAZING.

Wait, how many things can you equip at once?
Chest Piece
Boots
Gloves
Head Piece
Ring
Necklace
Shield?
Or can you equip an amulet and a circlet at the same time?