We moved our daughter at 15 months, but she was ready. We didn't give her a pillow until she was about 17 or 18 mo, but she did great with it. I would take it slow and see what he likes. If he wants the pillow then let him have it, I would start out with a smaller one though instead of a normal pillow. He will do great, but just be prepared for a little unease from him as well as yourself his first few nights. He will also probably slide out of the bed, but I wouldn't really worry as toddler beds are really short and if you have carpet it won't really be an issue.
With our daughter we made a big production out of the crib to the toddler bed. She picked out her sheets as well as the bed. Make it fun and let him set in the bed for a while before you put him down for the night. When he wakes up in the morning give him lots of praise for being a big boy.
at 3:56 PM on Aug. 26, 2009