Last time I did messy in a school uniform was actually a few days ago. I wore a Japanese style sailor outfit with a mid length skirt and heeled boots. It was very cute and sexy!
I have gotten messy in a school outfit for my then girlfriend -- I wore my school's polo shirt, khaki pants, etc while she wore her old high school uniform. It was a lot of fun but the mens uniforms are fairly generic. Even for work I usually wear a polo shirt / khaki combination.
School uniforms has to be one of my favorite out fits to wear as a kid. I did try bathing jeans and a white T-shirt to begin with and then moved on to my school uniform shirt, tie, jumper with blazer. 3 layers of messy clothes feels much better to wear than 1 layer.
I love school uniforms! I havnt got it wet or messy yet but i have put a uniform together that is close to how i remember from school and i think it looks pretty good