I have at least one thing from when I was ten, probably earlier. There's a velvet hoodie I have that I thought was ugly as a kid and it didn't fit me so didn't start wearing regularly until a few years ago. It's in perfect shape, fits great, it's not sloppy looking. I don't like casual hoodies.

I have a skirt that's definitely a kid's size but I like my skirts to fit at the waist which it does. I also hated it as a kid and didn't wear it, it was typical evangelical floor length garb, denim and floral, tacky as heck, but by the time I started wearing it it was tastefully vintage and ironic.