I had a real issue with ds and shoes, as everyone at primary wore black trainers, and he couldn't believe that he needed real shoes. Once he got there and saw that everyone else had real shoes he was fine.
To be honest, any black shoe will do, they wear all sorts. But this year (year 8 ) ds shoes are technically not allowed, they are plain black addidas. He says lots of the boys wear them, they don't look like 'trainers' but they are definitely borderline.
He also has long skinny feet and now he is a size 13
Also, he has been wearing skinny black jeans all year (ignoring the perfectly good black school trousers hanging in the cupboard) but they have recently had a big clampdown, so only proper trousers allowed now. We are searching for some super skinny ones for Sept!