Potty Training Success; When to Go to Underwear?

Now, perhaps! To continue it to be "positive", just don't make a big deal of it if he pees while wearing underwear- that will keep things going well. Change him quickly and say "better luck next time!" or something like that and move on.

My kids LOVED picking out their first pairs of underwear at the store. One of them really took to a neat-o idea we had about underwear: we got underwear that had kittens on the front, and we'd say to her "try not to get the kitten wet!" And it seemed like she loved having an additional reason to not pee in her pants, she made it her main focus to not pee on the kitten. This same child was the type to ALWAYS forget that she had to go until it was too late- the kittens helped her remember.

if he's been dry all week then go for it! i don't know how long your daycare requires him to stay in pullups (many will drop the price once he's potty trained so maybe they're trying to encourage you to keep him in them, but..) he's totally ready for undies. and get ready to "ooooh!" and "aaaah!" all over that cute lil bum once you see it in big boy undies for the first time. precious! (prepare for an accident or two but this is normal, just keep your positive attitude and he'll do great) congrats!!

Now, he is ready. There may be a few accidents but just do not make a big deal about it. It is too bad the day care requires pull-ups, can't he wear undies if you send extra cloths just in case (that is what most schools do). Having to wear a diaper at school could make him feel like less of a big boy or untrusted to do a good job.

How long (and why) is the daycare going to require him to be in pull ups?

It sounds like he is ready for underwear!

I don't know how old you son is. My son is 4 and is finally potty trained in the day and in pull ups at night (he was 2 months shy of turning 4 when we went to underwear). But he was in pull ups for a really long time (18 months) while I had a second baby and we all adjusted. My son is in preschool at a place that does daycare and they helped with the potty training once we got it started at home. The teachers have all the kids take regular bathroom breaks.

He is ready and it sounds like you did everything just right. At home, put hime in undies. He will still have an occasional accident, but this is completely normal. Once he stays dry for a week or two at home, I would put some pressure on the daycare.

I would suggest that you take him to the store with you and let him pick out some underwear because big boys get to do things like that. I think he is doing great!! Big step for mom and boy!! Let him be independent and take the reigns.