My great grandson won his school fancy dress day with his James and the Giant peach costume, he had forgotten to tell his Mum that it was dressing up day until that very morning, so, she grabbed some cardboard and string, made him a sign to hang round his neck, which read 'MISSING - One Giant Peach! If found please call......'
He won first prize and there were some blooming expensive costumes around then apparently.
I think these days, without wanting to spoil your child, you do have to think about them being bullied. If you send your Wise Man to the Christmas Nativity with a Great Yarmouth Tea-towel, well, back in the 80's that was fine, but these days, you will have kids looking down on them, and yes, you shouldn't do things to 'please' others, but you still have to pick your battles as it were.
My daughter works, has four children, and believe me, does a heck of a lot more things with her children than I did.