Shoes & Sox were good for me... I got DS some when he had been walking for two months, and I only got them for daycare, as she likes to take the kids to the park. I cant remember the brand, but they are all leather, with a flexible sole. Clarks had the stiff sole, and I will probably get them next time. The shoe fitter suggested to come into the store monthly or 6 weekly to get his feet measured. They also do a buy 6 get the 7th pair free (i think those numbers are right) so it does make the $100 per pair a little easier to take...

But saying all that I make sure DS has plenty of shoe off time, and he helps with that, taking his shoes off at any opportunity he has .