Toybox is roughly the same size as a Buld-a-Bear, and I was inspired to draw him in little outfits
Also wanted to show that he is capable of being bipedal or a quadruped (hence the sploot he does in the pajamas)

also in AestheticVerse I imagine he'd had outfits matching with Esme, especially when she was younger. (jesus I need to draw/get art of them together)

also yes he likes dresses