I think Luffy would be the kind of kid that play dress up with his mom's things, like he's in a catwalk wearing heels to big for his tiny feet and smeared makeup and maybe even using a towel as a placeholder for long hair.
But than I remembered that its not mom, its Baba! and now i cant stop thinking of Luffy dress as a mob Boss with a fur coat that is 3 times his size and a lolipop for a cigar while his best Crocodile impersonation, It would be so cute!!! (And of course If Dragon saw he would be weeping about How cute his kid is, Of corse 🙂↕️.)
Hahaha, yes, I guess that by the time Luffy's old enough to play dress up with Baba's things, Crocodile probably has disposed of the things he still had when he was, sort of, playing pretend as a civilian mother.
(Of course, this depends on the AU. In Stinky Child AU he probably doesn't have any clothes from his younger years that he is attached to, because he's always been favoring trousers and shirts. In a Kuja!Crocodile AU he might keep something as a memento? And Luffy could get into that box.)
But yes, I approve of Luffy dressing up as a mob Boss. Dragon would love that (but I think Crocodile would too~)
Don't have time for art right now, but I'm putting it on my mental to draw list >w<