I picked out 6 different pairs of boots at Zappos for my 4-year-old daughter to try on (thanks, Zappos!). Out of all of them, she liked these the best. She can be pretty picky about comfort and these were the only ones with which she couldn't find fault. They look great with knit tights and a skirt or over skinny pants or leggings. My daughter is somewhat stocky and these fit with room to spare around the calves. I haven't weatherproofed them yet, but they have so far held up very well to the abuses of the playground. I hesitated to spend this much on boots for her, but I like the fact that they're all leather and it's important to me that they're flexible and comfortable on her.