From the time they start standing/walking to the age of 3 their feet are developing, and it is super important to get very flexible shoes. The best I have found are those soft slipper pull on types like Robeez (also have a target brand for 12.99) for nice days or indoors or bare-feet are best. Then for good outdoor shoes See Kai Runs, a bit pricey, they have sales sometimes on zappos, but those are the best I have found for flexibility. They are super comfortable and my daughter loves hers. Another option, are Simple Kids, not as flexible as See Kai Runs, but pretty good and a better price, and they are made from recycled material. Hope that helps. You'll be able to find them all on zappos. :)