Even if he doesn't dress up often, it's always good to have a pair of boys' dress shoes on hand for occasions when sneakers just won't do. Here are a few styles that will be well-received by parents and kids alike.
A loafer is always a good bet in dress shoes for boys, because since there are no laces to be concerned about, they tend to stay looking neat. Generally speaking, the shinier the finish, the more formal the shoes will look. These loafers from Kenneth Cole will work with everything from chinos to basic suits.
If it's a very formal, lace-up shoe you're after, these shiny "Delmon" oxfords from Venettini should do the trick. At around $85, they're a little on the pricey side for shoes that may not get a lot of wear, but they're a good example of classic boys' dress shoes -- and similar versions can be had for less.
Sometimes it's wise to look for a dress shoe that is versatile. Stylish slip-ons like these "Cash or Charge" loafers from Kenneth Cole can lend a dressy look to jeans or a slightly casual feel to suits. They're a good example of all-around, multi-purpose dress shoes.
When it comes to boys shoes, there are times when you may not something too dressy, but you just want something other than a sneaker. Slip-on or lace-up shoes with rugged soles, and interesting textures can make jeans and cords look nicer than sneakers would, and they'll likely be met with more excitement than really formal footwear. I love these suede oxfords from Jumping Jacks.
Unlike men's boots, it'd difficult to find boots for boys that are dressy enough to work with a suit. However, there are several styles that will dress up a pair of jeans, khakis or cords as well as shoes, while still providing all the protection and durability of boots. Styles like these lace-up boots from Dr. Martens are a popular choice among parents and kids.