My kids are still fairly young, with the oldest being only 9, so children's fashions hasn't really much of an issue with them yet. We do have the oldest, Aaron, who has Asperger's and goes through phases where he wants to be in a costume, or "dressed" up in "fancy" clothes, and then swings the pendulum where he hates those clothes and only wants sweats or even pajama pants. We've been fortunate since we've home-schooled him for a while that we've been able to accommodate him, and his therapists and specialists understand.
However, now that he's beginning to go back to school, we are having to work out acceptable school clothes. He will be in a resource room, so it isn't a huge issue what he wears, and they are willing to let him wear whatever he's comfortable in, but since he had the issue of being picked on previously due to his special needs, we don't really want to call unnecessary attention to him from the other students in "mainstream" classes and subject him to taunting. I've been showing him some sites featuring boutique kids clothing and various styles of fashions for children to get him an idea of what kids his age are wearing, to see if something catches his eye.
He went to the school today for the first time for a test, and it was his first time being back in a school without me since the trauma 3 years ago. He did very well and was excited to be there. I think he talked the therapist to death, she was very impressed with his vocabulary:) Since he was in a room with just the one teacher, and I knew I'd be leaving him alone, I wanted him to be comfortable, so I let him pick out his own clothes. He chose dress pants, a button down shirt, a tie, a vest, and a suit jacket. A little formal for 3rd grade, but he was happy, so we went with it:)