Skinny is the easiest. Pretty much any shoe, from a flat to a gigantic platform to a tall pair of boots works. The thing to remember is the skinny really features the shoe. Skinny pants are like two long arrows pointing down at your feet. So feature some fantastic shoes! Flats look great with cropped skinnies, though you can also leave them long. It's purely a matter of which look you like better. Leaving them longer will, in theory, make your legs look longer, but showing some skin by having them cropped can be really flattering too. (The only way to have it both ways is to leave them long and cuff them every so often.) If your boots are gigantic you can tuck the jeans in, but the fashion department is iffy on this last bit.
Illustration by Lauren Friedman