It's not a bug; any kind of helmet usually occupies both slots as they sit on the head and face at the same time. Any Season Helmet, Statue Mask, Crabby Helmet etc. are all pieces of gear that take up both slots.
Why are the items you listed then only visible in the Hats category? It might not be a bug but it's an inconsistency for sure. My guess is that they started off with putting them in both categories but later decided to only put them in the Hats category, as the Jumpkin Mask is the first mask they added I believe.
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