Yeah I don't have any sneakers that can cut it I think. The rest of the look is pretty sweet, especially the last iteration with the edun t-shirt. :'(
Maybe any of these Warning: Spoiler! (Click to show)
I feel like drop crotch is difficult to pull off, but perhaps the tendency to look diaperish can be moderated with a very long shirt with a bit of drape. It seems like the tee worn only drapes nicely at the expense of adequate length. Also I would say no to that footwear.
What I'm really trying to say is I feel like dropcrotch only looks really good to me when styled to look like a highstreet tall tee and sagged pants, while actually being able to wear the trousers at a comfortable height.