These are the reference images that influenced my designs.
Character: Rich kid updated designs
Since the previous design for the rich dorky kid looked too grown-up and casual, I was advised to try with a bit retro school uniform. I tried to make the designs as realistic as I can so the kid could look as overdressed as possible. I did find it hard to make the uniform fit the young child, so I had to go for the shorter pants even thought I do find the length I bit weird. I'm aware the drawings look a bit awkward but this is mainly base so I can pick the final idea.
After I played around with colour I think the only design that fits best for me is #5 and I should maybe try it with the colour scheme from #4. Designs #1-3 make the kid look rather older/too serious and modern. I do find #6 cute, but I don't really think it fits.