For one thing, this is a toboggan.
And this may be a beanie, a non-serious piece of headgear
That aside, I really want to tell you that I sometimes wear a toque in bed. Well, not really in bed but in chair on a cold night. I don't wear it to go to sleep exactly, but I leave it by the side of my chair and sometimes grab it in the middle of the night because we let our house get quite cold, and I have a lot of bare scalp up there. Those who have a nice head of hair probably don't appreciate just how well it insulates your head.
When I settle in my chair on a cold winter's night, I decide between donning my hoodie or engaging my heated throw. When I opt for the heating, assuming I remember, I place my toque by the side of my chair just in case my head gets chilly while the rest of me is comfy cozy. Come 4 or 5 o'clock when the house is at its coldest, I may reach blindly for the toque.
That is what this silly, old Canucklehead has to do in his silly, elder years, and yes, that is how I sleep, or try to, non-horizontally in my recliner. I think it is the ledges (arms) on which I can use to prop my legs that make it better for me than a flat bed











