OC asks, if you wish to...Rob 'Em Iwerks, 32 (as of post-fic) and 50!
For those of you who don't know my trash pirate son Robert "Rob 'Em" Iwerks, you may meet him through reading my Disney mega-crossover fic, TrueMagic: A Disneyland Fairytale!
32. What do they dress like? What sorta shops do they buy clothes from? Do they wear the fashion that they like? What do they wear to sleep? Do they wear makeup? What’s their hair like?
Well, of course while in the Kingdom of Dreams, Rob 'Em dresses like a pirate (tricorn hat, long coat, leather boots, and all). When he goes to Disneyland as a guest, his clothes are super casual and kind of worn. Jeans, well-fitted T-shirts, white undershirts, baseball caps, leather jackets, and flannel shirts are his Real World aesthetic; Rob tolerates sneakers and sandals, but he'll probably always be most partial to boots. He wears an eyepatch rather than his usual bandana while in our world, and he also often wears fake military dog tags around his neck: one of his "Friends" suggested them to him, so as to give other people less reason to question why he's missing an eye. Rob 'Em doesn't wear make-up, but he does have a pirate "P" brand on the inside of his wrist and a tattoo of a large sparrow on his shoulder (in honor of his not-so-great quasi-father figure, Captain Jack Sparrow). His hair and facial hair has always been shaggy, but since he became a Cast Member, he's had to keep both much more trimmed.
50. If they could only take one bag of stuff somewhere with them: what would they pack? What do they consider their essentials?
Rob 'Em never goes anywhere, whether in the Kingdom of Dreams or Reality, without his ship (which he can shrink to a small size and wear on a chain around his neck). While in the Kingdom, he always has his pistol and cutlass on him. Post-story in the real world, he'd bring the shield Merlin gave him (which can be shrunk to the size of a coin so he can carry it around in his pocket), his Cast Member ID, maps of both Disneyland and the Kingdom of Dreams, a compass, a calculator, and the pin lanyard Marcia bought him.