I always buy ahead when I find good sales. I would never put them into shoes that are more than a half size off their current one, though. It's uncomfortable and dangerous.
Larissa
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DS has giant feet...LOL, sorta. He just turned 14 months old, is in a 6-6.5 (I'm sure it won't be more than another 2 months before we move to a 7!) Since about 6 months old we've moved him up a size about every 2 months! (He could wear a 2 at 5-6months, so he's grown nearly 5 sizes in 7 months!!!)
His feet are also very wide, and thick. He can't wear sandals at all, and even his crocs make light marks on the top of his feet. I don't know what I would do if I hadn't bought ahead (and saved some of his brothers shoes). Just pay attention to the width, and I would even try them on now if they're just a size or 2 bigger to make sure there's enough room for wide feet.
BTW, we LOVE stride rite! I only buy them at resale shop though, I'd rather have used stride rite than cheap new shoes.