When I was little, I could not STAND to have the lines on the toes of my socks not completely straight! I mean, sometimes my mom would put them on me 3 or 4 times, I would freak out! I did find out as an adult that I have adhd, but not sure if that was the problem or not.
My daughter wants to wear what she wants. She is almost 8 now, but she did the same at 5. She wants stripes with plaid, tutu's with jeans and tank tops in the winter. Being that she is my 3rd child, I have learned that what she wears is really the very least of my worries. As long as she is dressed for the weather, I let her wear what she wants, within reason of course.
One idea is to pick out 2 outfits, and let him choose what he wants out of the 2 outfits. He can mix and match them. Tell him you understand that he is a big boy now and that you know he would like to pick out his own clothes. And he can, but only out of those 2 outfits. I think this should work well, maybe with a little time to adjust. Be firm, only the 2 outfits and that is it.
Good luck!
R.
I am a 45 yr. old mom of 3, I have worked outside, inside, and been a stay at home mom. Right now I am at home, but about to start at our local school very part time. Husband works 7 days per week though.