My son is 9 and still wears his shirts backwards, or inside-out. I have a cute picture of my sons in which Q is wearing his pants backwards(elastic waist with a dummy fly)! We never noticed it that day, we only realized it when we got the film developed!
Like you, redhead, it's 9 x out of 10. I don't know the "why", but I would guess he has more important things on his mind. Even when we bring it to his attention, he doesn't care to correct it. He nearly always sleeps in backwards or inside out PJs. They say "pick your battles," I usually let the PJs slide.
I do that constantly check your shirt, make sure his fly is zippered, underware on right. He's 9---it's like i have to watch over to see if he get's dressed right, it gets tiring and i want to yell at him, but i try to be patient, i know he's not thinking and in a hurry.
Redhead,
I have not had this particular problem with clothes on backwards (but I did teach my kids early on that tags go in the back). And I'm not sure there's a particular significance except possibly inattention to details. One problem I did encounter with my ADHD son when he was younger was putting shoes on the wrong feet. I solved the problem by painting a dot on the inside of each shoe or boot. I then told my son to "match the dots" to get his shoes on the right feet. It worked! Maybe you could color a dot somewhere inside his clothing (like the front) and then tell him where to place the dot. Just a thought.
HAS ANYONE EVER EXPERIENCED THEIR CHILD PUT THEIR CLOTHES ON BACKWARDS? I MEAN ALL THE TIME---IF I'M NOT THERE WATCHING HIM 9X'S OUT OF 10 HE PUTS THEM ON INSIDE OUT OR BACKWARDS. WHAT DOES THAT MEAN IF ANYTHING?