I bought a woman’s handbag decorated with Minnie Mouse to carry with me while I was at WDW. I bought it because it was perfect for my needs and because — damnit! — I liked how it looked.
I felt utterly unself-conscious carrying it around because, well, it’s Disney World, which is surely one of the safest places in the world.
I wasn’t aware that I was getting funny looks from anyone, and the saleswoman at the store on Main Street where I bought it was delighted with me making the purchase.
So if your grandson wants to wear a princess dress, then good for him. It’s 2017. People can be who they want to be, especially at Disney World. And I think it’s terrific that you’re facilitating this. Good for you!
(PS I gave it to my friend after our trip. I’m not confident to carry the bag round my home town!)