shout-out to my Smartwool beanie with the covered openings in the side for glasses arms. mine also has an opening in the back for a ponytail, which it looks like they don't make any more, but you can still get the glasses one. i am not sure if it fits small heads though.

(edit: the ponytail one is "women's" and so i think it runs a little smaller. it is just small enough to fit me. the "men's/unisex" one is probably larger.)