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A Short Skirt or Dress
Okay, so I am going to ease you into this with the simplest option of the bunch here. Since this skin-showing style already makes legs look, well, leggier, you don't need worry about taking extra steps to stretch your proportions. Pretty much any kind of flat shoe will work: oxfords, sneakers, sandals—whatever! Just go for whichever you like best because there's not an unflattering choice out there.
Like short skirts and dresses, most comfortable footwear works well with shorts, too. There are a few things to be careful of, though; for instance, ballet slippers aren't going to work, as the style's too tight and flimsy. Wear a pair and you run the risk of looking a little bit stumpy (especially if the shorts are extra-long or extra-short—those extremes need a sturdier shoe); it's better to go for something with a slightly thicker sole and more structure, like a sneaker or espadrille.
Wide-Leg Pants
I'm going to be straight with you here: I don't advise wearing flats with wide-leg pants if it can be avoided—it's very tricky look for even the most genetically gifted. However, if you must, try to make the shoes as close to your trouser's color as possible! It elongates the leg.
Maxi Skirts and Dresses
There's no way to wear a maxi skirt with closed-toe shoes and not look like (a) You just escaped from the kind of religious sect featured in Big Love, and (b) You shrank four inches. The good news, however, is that any kind of sandals work, so once you've got the formula down, it's hard to mess up.
We're talking about slim-legged jeans here, because the only flats that bootcut denim works with are flat boots (duh). Anyways, although most of your heel-less shoe wardrobe will work with straight or tapered styles, try to wear your skimpier footwear (like tight ballerinas or nearly-naked sandals) with skinny jeans and sturdier oxfords, booties and sneakers with looser cuts. A good rule to remember is that the more fabric there is, the more substance you need to balance it out.
Mid-Length Skirts
If it hits anywhere between the knee and ankle, you want to wear an ankle strap. Don't worry if the shoe itself is a sandal, d'Orsay flat or basic ballerina, just make sure that extra hardware is there and your ankles will always look daintier, your legs more streamlined.
Cropped Pants
Out of all the styles I've warned you not to pair with ballet slippers so far, this one might be the most important! Mid-calf trousers already make even tall people look a little bit shorter so you need to use every trick out there. That means picking a menswear-ish flat with a hefty, substantial sole to fake whatever height you can.