Scared of Underwear!

Start trying putting the underware over the pullups and then maybe under the pull-ups if he will let you then eventually wean to no pullups. It's worth a try.

My first thoughts were..Let him wear the pullups! If you talk to the preschool they will understand as long as you assure them he is fully potty trained. If they don't then I'd find a new preschool!

Thinking a little more, pull-ups are expensive and reward charts might work (7 stickers equal a trip for ice cream or small prize he'd really like). When the package runs out you could say very simply either the store was sold out of pull-ups or you didn't have enough money after buying his fav food or something. Then he can choose to wear underwear or nothing. Encourage your older kids not to make fun of his decision.
Good luck :-)

I realize this is going to be total opposite of what some other people have said, but...

my son, who seems to be afraid of EVERYTHING that is new to him, did not want to transition to pull-ups from regular diapers. What I did with him for that was every time we needed a diaper change, I asked do you want a pull-up or a regular one. Every single time, I would just calmly ask him and let him decide. For about two weeks straight, every single time, his answer was "regular". I just kept asking him every time and eventually he answered "pull-up" one day. For another three weeks or so, he would say pull-up sometimes and regular the rest of the time, until he was mostly asking for pull-ups. At that point, I quit giving him an option, and he wore pull-ups all day except for at nap time and bedtime. He is happily in pull-ups all the time now except for naps and bed.

I fully intend to use the exact same strategy when it comes time to transition to real underwear for him. Ask him "do you want a pull-up or underwear?" Respect and honor his choice.

My philosophy is kids around that age (and actually EVERY AGE, including adults) just want to feel like they have control over their own lives. It is a small thing to do, giving them a choice about what to wear for diapers/underwear etc, but it makes a HUGE difference in their eyes to be allowed to make a choice.

Now some kids don't care what they wear. Some kids won't fight you if you don't give them a choice. But some kids (seems to be the sensitive ones from what I have seen) just need to feel in control of stuff like that.)

I give my son choices with LOTS of things. The things I do not give choices on are mostly safety issues. He does not question me on those issues. And he does not usually question me or fight me when I don't happen to give him a choice on some minor issue that I usually do give him one on. I really think he obeys fairly well because I give him choices whenever I can and he feels at least somewhat in control of his own life.

Sorry I got so long-winded- I do feel pretty strongly about the giving choices thing. My main thought for you is that it will be a major battle for you if you try to force the issue and could majorly backfire on regressed potty-training issues when it becomes a power struggle. Giving him the power to make the decision will make it easier for both of you, I think.

How necessary is underwear anyway? Is it a requirement for Preschool that he wear them? I say let him try it all natural and I think he will WANT to wear underwear after the first time he gets certain things bumped, etc.

I think Pull-Ups are fine too - maybe he is scared that he may not make it to the potty in time and wants other options - I think your Doctor is correct to say to let him gradually switch on his own.

You may also consider a prize or special treat if he wears underwear for even a short while ...

My first thought is... don't give him a choice. He's 3 1/2, he should be in underwear full time and independent in the bathroom by now! When you put out his clothing in the morning, put out pants, a shirt, socks, and underwear. Direct him to his clothing and tell him to get dressed, end of discussion. Making it that big of a deal by buying tons of undies and still letting him wear the pull ups in exasperation is making it a battle, and he will continue to do this until you just stop the back and forth. Mark it on the calendar... as of Monday you will no longer wear pull ups, you will wear underwear. STick to your guns, there are no more options but ot put the underwear on.

You might try a weekly reward chart. Each day he wears underwear he can put a sticker on his chart. When he works up to wearing it for a whole week he can choose something special. A visit to somewhere he likes, a special dessert, extra stories at bedtime, special time with mom or dad, a small toy...

I had the same issue when my daughter was that age. She hated wearing underwear. What worked for me was pretty simple, I had a neighbor that worked at the YMCA where she was going to be attending pre-school, and my neighbor (that my daughter looked up to) told her she couldn't go to school unless she wore her underwear. I also took her to the store and let her pick out her own kind with Dora or Princesses on them, whatever she wanted. I also made sure they were big enough so they didn't feel so tight on her. Good luck, this is just anyother fase that they will soon out grow!

Oh honey, don't take this the wrong way, that is totally hilarious because I thought my son was the only ONE!!!!!!
My suggestion is to take him out for his brand new school big boy pants that he will get to pick out and wear to big boy school! A special one on one shopping trip just for him. I mean hype it up with the expectation of like christmas. Get him geared up a week before hand, count down the days on a calender, anything you can do to make this a HUGE deal. by the way, he is scared of certain ones, but it will take forever for you to get it out of him ( I know, I sat through 1 1/2 hours of uno with Avery to get the story)once you get to the store let him pick them out. make oooohs and ahhhhs over every single one he firmly decides on. remind him that these are the type only for big boys going to school to wear! I know it sounds crazy and you'll be catering to him a bit. But I bet is solves the problem. Unless he is more of a boxer fan. ( my oldest had the same issue too, we 6months after his shopping trip had to go back to get boxers, cause his new ones made him "itchy and squishy") Good luck and please tell us how its going!! K.

You might be able to enlist the help of your 8 yr. old. Your youngest might look up to him. If your oldest starts talking about how 'cool' the Thomas the Tank Engine or whichever undies are then maybe your 3 year old will get excited about them. You might have to go to the store with both kids and just have your 8 yr. old stand there and get all excited about some new underpants! Let him know that he is being such a big help with his little brother. If your youngest still is not thrilled with the whole idea then let him wear the pull-ups to preschool. He doesn't need the added stress when he is beginning school. He'll eventually wear underpants... I don't think he'll be 10 and saying he doesn't want to put them on:)

I am not sure what all oyu have tried, so here goes. I would take him shopping with you and try to get him to pick out some. Otherwise, try putting the underwear on over the pull up and then eventually switch (this worked well for my daughter).