I know the answer to this is simply 'when they can do it properly', but its not always that easy! My DD (3) now insists on doing her teeth on her own. She is actually pretty good at it, although obviously nowhere near as thorough as I would be. She has got so independent about the whole thing that the options are that I either let her carry on doing it herself, in the knowledge that it might not be amazingly thorough but it is a learning process, or I forcibly do it for her which would involve basically holding her down while she screamed. We have had to do the 'headlock' style of brushing in the past, and I understand that it can be necessary, but surely you have to give them a chance to try their best on their own at some point?????