How do I help my little one transition to a new school and manage his modesty?

Question

I have a question regarding change of school:
When should we start to prep him for this knowing he leans on anxious?
Do you think a transition book would be helpful again?
He is familiar with the school since he has been there for one whole year...

Also, regarding summer camp, I took him out of the second camp today. He really didn't want to go back after I picked him up yesterday. We found out it is for ages 7-15! No one told us before.
Yesterday he was just sitting around, not wanting to go into the water (and it was a water sports camp!). Later he told me it was because he didn't want to get wet and then change clothes in front of everybody as he didn't feel safe. I had told him several times in the morning that I wanted him to change if he was wet and felt cold (at least the shirt, the bottom could stay wet if he felt better about it), and he said that having this in mind, when he was at camp, he would rather not get wet and follow my instructions than getting wet and having to change or "disobey" me and not change (I felt so bad to hear this). He is already a bit shy to change in public compared to other kids his age (in our opinion, not sure if true), like he must have a towel completely around him when changing at the beach and no one can see anything. And he even feels embarrassed to change just his shirt. How can we help him to feel more comfortable?
We understand getting changed completely in public maybe isn't comfortable, but the T-shirt at least, in public?? My husband sometimes even walks those few minutes to the beach by our house without shirt, Gabriel really does not feel comfortable doing that. Inside our 4 walls he is not shy at all. Thank you!

Answer:

FOR SCHOOL :
If he will be going to the new/old school you would start talking about prepping him about it in August a couple of weeks before school starts. The prepping consists of making sure his sleep, eating and routine is as close to the routine he will have for school. The Friday before the week of school have a "dry run". Pretend its the first day of school and do the morning routine, including driving to the school to "play" going to school.
This "dry run" does two things for kids:
1. Lets their brain have a memory, a "fun" memory, it will use for the day of and..
2. It gets the kinks out for the actually first day of school.
You could do a transitional book but its not absolutely necessary.
Your son will have lots of questions, make sure to answer all of them. If he repeats some of them and you have already answered twice, say to him, "buddy, do you remember what I said about that last time?" Then wait for him to answer.

HIS NEW FOUND MODESTY:
Yes this is perfectly normal for children 4.5 and older, they begin being modest of their naked body. Always follow his lead and let him dress and undress in the way that he feels comfortable, no pressure. This builds his sexual safety and his sense of consent. If he doesn't want to have a bare chest like his dad, its fine, respect it. That way if someone else is crossing a boundary with him and his body he will know it is wrong, because he has experienced with you that you respect his modesty, his body and how he wishes for his body to be seen.

Also make sure to teach him how to dress himself in all the different types of clothing (I.e. uniform, weekend clothes, bathing suit, etc.) This helps him feel safe and helps him to continue to have ownership of his naked body.