I'd go with TomD's suggestion--start with the hat!

I used to sleep in the next day's hiking socks. Last spring I bought a pair of fleece socks specifically for sleeping. They are so soft and cuddly that my feet sigh with gratitude when I put them on. And the next day's hiking socks are not stretched out of shape before I start hiking.

I have to get up several times each night, and find that it's better to have something on my feet that my shoes (or Crocs) will fit over. I wouldn't want to walk on the wet grass in booties and then put the wet booties inside the sleeping bag.