Aww, I think its cute that you had a favorite hat, no matter how gawdy. I cant think of any clothing items my kids have been like this with, but just in general my girls can be goofy when they play dressup. They dress hodge podge and try to be fashionable and it does make me laugh, but I love that they are trying to be creative and express themselves. If they did have a goofy, gawdy hat that they wanted to wear everywhere I would be all for it. It's all about self expression and I think it boosts their confidence.