Wearing flats over wedges or heels, I generally wouldn't advise, simply because they are not as flattering on a woman's leg. But flats do have their place in a stylish fashion wardrobe, especially when running errands on the weekend or if you are going to be walking for a while. The d'Orsay flats that have flooded the shoe market in recent months have become a favorite for even the pickiest fashionista. They have all the comfort of the standard ballet flat, but showcase an interesting cutout and a pointy toe to help elongate the foot (and the leg line). The Jenni Kayne version is the most coveted because of the interesting material choices and heightened quality; however, many other brands have developed similar versions for a fraction of the price. So, if you are on the fence about this trend, investing in a less expensive version may be the way to go. However, as with everything, go for as much quality as you can afford.