When it comes to clothing, I've never had much of a problem with self-expression. In fact, on my wedding day, my father reminisced about how I'd go to school wearing trousers, a skirt, and mismatched shoes and socks. I enjoyed my unique style, and I still do.
My children seem to have inherited the knack for self-expression in their clothing. Kieran often intentionally wears his shirts backwards and/or inside-out. Charlotte refers to certain shirts as "styles". She may not be able completely dress herself without help, but she is very opinionated about what she wears. I enjoy seeing their personalities expressed in this way.
However, it seems some don't appreciate it. When out-and-about, people sometimes comment about Kieran's choice of how to wear his clothes (Charlotte, being younger, doesn't seem to get the comments). My motherly desire to protect my child means that I can have a hard time with such comments. I don't want my child to become self-conscious or uncomfortable about his unique sense of style, but neither would I want him to conform just because of comments. I don't want to fight his fis for him, but I need to give him the tools needed. Perhaps I can stick with saying something simple like "that's how he wishes to dress" and telling him I appreciate his unique sense of style.
Actually, this reminds me of walking with Kieran through Liverpool. For a while, he'd suddenly declare that we needed to do a silly walk or a dance walk. So there we were, turning heads with our silly walking (we could've been on the Monty Python sketch). I know we got funny looks, and I'm sure people wondered about us, but I have to say that it was more fun than just walking normally, and I will cherish that memory. We no longer walk everywhere, which I miss, and now he's moved on to a new form of self-expression. I will cherish this moment, as well.