I love Pediped shoes for my babies. Their Flex shoes are perfect for toddlers who are very capable walkers (I never tried their pre-walkers). The sole bends so easily and they feel like they're very cushioned and therefore comfortable to walk in and the fact that they're machine washable is amazing. But the BEST part is that they come with an extra insole. This means you get so much more for your money! Instead of dropping $35+ on shoes your kid will grow out of in a couple of months you buy a size up and put the extra insole in, it makes the shoe fit. Then, as their feet get bigger you take the insole out and the shoes still fit! It's like getting an extra shoe size for free!
With this brand I would make sure to go to their site and print off their shoe measurement guide - the ranges are so different from brand to brand that it's easy to get a pair that are too small for your kid and be stuck playing the return/reorder game. I learned this the hard way but finally getting the right size has been worth it!
This specific style (Adrian sneaker) is very cute on little boys and works well with casual and dress clothes, they also hold up really well to tons of scrapes and many machine washes, which is important with the cost of kid shoes.