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And I have tried stocking up on shoes, like stride rite for Target, when I see them on clearance but I have the problem that my kid’s feet grow really slowly so I risk buying the wrong season. But if you see the Surprize stride rite ones for less than $10, definitely pick them up.

We always start with the soft soled moccasins. Robeez, or other like brands. For DD1 I actually found a great in-between sofe/hard soles called Jack & Lily. It's got another rubber layer so it was more sturdy, but still super flexible. I got them on Zulilly.

Then we went onto sneakers or Stride Rite.

@nutmeg36: I have put mine in them without socks. I guess it depends. It was late fall/beginning of winter when both my kids started walking so I could get away without socks for quick trip outs. I see you're in the NE too; as long as they're comfy, personally I'm okay without socks...

I forget to add for DD2 had a pair of minnetonka (sp) fringe suede moc's (I got from Nordstrom) and they were super cute/sturdy.

DS2 wore Robeez in the 6-12 month size (the 12-18 month size is HUGE!) for a good long while - like until 16 months old? Then we finally got him some Stride Rite SRTs on sale (I only buy them on sale) for about $20-25 bucks.

I generally like to get the first pair of sneakers in the store to size and try on because turns out both my kids have wide feet and they had to wear much bigger shoes than the size you'd wear based on the length of your foot alone. But I wait until they are confidently walking well.

You can get nicely used kid shoes on eBay for $10-15 bucks once you know their sizing. I also sized up on a pair of Keens for DS2 last summer (he was a size 5 then but I got him 6s) and he wore them big last summer (since the ankle strap cinches) and he fits them fine currently. I think they should (fingers crossed) last most of this summer because you don't wear socks with them and they're generously sized and wide in the toe.

I don't like all-velcro strap shoes at this age. They like to play with the velcro and take off their shoes constantly because its fun. Rather, I like a shoe that has the elasticized laces that you slip on to the foot, with a velcro strap at the ankle for a secure fit. That way if they play with the velcro strap, the shoe will still stay on.

All velcro shoes are just useful now at DS1's age (3.5 years old) because they can put their shoes on and off themselves.

DD1 wore mostly moccasins until at least 1.5 and they last a while because the soft leather stretches. She wore them with and without socks. I have some new moccasins for DD2 (8 months) because DD1 wore them out once she started walking everywhere and I also bought some Piper & Finn oxfords for nicer occasions (they're $$ if full price but sooo adorable - I bought on clearance).

The only shoes I buy more than 1 size up in are tennis shoes (we liked New Balance once she was running around) since they generally wear tennis shoes year-round and eventually the Old Navy jellies since she wears them all spring/summer/fall (but we're in the south). I get the jellies on sale/clearance so if we can't wear one pair, I'm only out like $4.

I feel like I wasted a ton of money on shoes, my son didn't do well with the Robeez soft soled shoes because his foot was really thick, so I brought him to a specialty kids shoe store just to get an idea of what was out there and what size he truly was. We did the best with athletic sneakers when it was all said and done.