Chances are good your son wants to spend all his time in sneakers or flip-flops, but you and I both know that there are going to be times, especially during school hours, when he’ll need to concede and slip into a pair of boots, casual shoes, or even — wait for it — dress shoes.

To make the whole process a little less painful for both of you, I’ve put together this list of styles to consider when shopping for boys’ school shoes, along with a few suggestions for choosing each of them.

Boys School Shoes

Boys’ Sneakers and Athletic Shoes for School

Selecting a pair of sneakers for your son will probably be one of the easiest decisions you’ll have to make. Let his personality and activities dictate whether you go for a more rugged, heavily padded sneaker, or one that can double as a casual shoe.

If you’re in doubt, and he has no clear preferences, take a look at what some of his peers are wearing. And, if all else fails, you can opt for a simple, classic sneaker. One that is free of trendy detailing, and extremely bright colors.

If your boy plays any organized sports, he’ll probably also need a pair of shoes specifically for that purpose, and depending on the school, he may also need a pair devoted exclusively to gym class or PE days.

Casual School Shoes for Boys

Casual shoes for grade school boys tend to land somewhere between a boot and a sneaker — which is cool because that’s probably the look he’ll want anyway.

Look for a shoe that is sturdy enough to allow for rough play, but a bit dressier than a sneaker. These types of shoes will give a nice, relaxed look without being too sloppy, and they’ll go with jeans as well as cords, and other casual pants, like khakis or chinos.

Slip-on styles are fantastic because, well, there are no laces to deal with. They’re easy to take off and put on.

They also give a nice, clean appearance, with no effort or your part, or his. However, if he finds slip-on shoes a little too tight or looses, and wide or narrow options aren’t available, then he may appreciate the fact that lace-up shoes (oxfords) offer a fit that is a bit more customizable. As do slip-on shoes with side goring.

Dress Styles for School and Extra-Curricular Activities

When it comes to kids in grade school, the best bet for dress shoes is saving them for very special occasions. That way, they’ll still look good by the time they’re needed. For the best fit, buy close to the occasion — or occasionally check that the ones you already have are the right size in case a “dress-up emergency” arises.

As a general rule, the shinier the shoe, the more dressy it will appear, but if scuffs are a concern, suede is also a great choice for dress shoes. Again, if keeping laces tied proves to be a task, you can opt for a slip-on style, like a dressier loafer.

Water-Resistant and Rain Boots

It’s going to rain, in fact, it’s going to pour. So, at some point, water-resistant boots are going to be essential.

How much storage space your child has at school will help determine whether you want a boot that can also be worn indoors all day, or one that your boy will change out of after arriving at his destination.

If he can change out of them, taller styles, like classic boys’ rain boots, are fantastic because they will also protect the bottom of his legs — as well as those of his pants.

On the other hand, you can save a bit of money and perhaps make your son a bit happier, by opting for a pair of hiking-styled waterproof boots. What they lack in height they make up for in versatility. There’s no need to remove them once your child arrives at school, and they look great with jeans and casual pants.

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