DD is the same age as your son. She's been out of her sleeping bag for about three months and since then I've had her under a quilt. I encourage her to "get under the covers" and she really enjoys that part of her night routine and feels very proud of herself. Often when I leave her she's back out from under the covers and standing up waving bye bye to me but when I check her later she's back under her quilt so I know she can do it herself which is good.

She's had a pillow for a lot longer - maybe 10 months but I'm guessing a bit. I started using it when she had a cold and thought the elevation would be good and used one of our full-size ones because I didn't have a special smaller cot one. I never bothered taking it out again probably because she looked so cute with her head on the pillow! Not a great reason I know.