Buying dress shoes for boys is always a parent’s worst nightmare. I dread taking my son to buy new shoes, because he loves to squirm around and after trying on a whole two shoes, he is ready to leave. And of course we all know our kids will tell us that the shoe is comfortable so they can get it over with. Then they turn around and tell us how much the shoe hurts once you get home. Don’t you just love that!

This is why we have compiled a simple guide for buying boy dress shoes:

Try to go shopping early in the week, during the day if possible. This is always the best time to shop because the crowds are small and the shoes sales people will have plenty of time to dedicate to you and your child.

Be sure that the salesperson measures both the width and the length of your child’s foot. Many boys dress shoes are quite stiff and if your son has a wide foot, they will need to be fitted in the proper shoe width.

Your son should try on both shoes, as many children can have one foot that is bigger than the other. As a standard rule, their toes should fit about half an inch from the tip of the shoe. Keep in mind that square-toed shoes will offer more room than the classical rounded toes.

Have your child get up and walk around. Pay close attention to their heels and ensure that there isn’t any slippage.

While it is tempting to save money and buy a bigger size, keep in mind that dress shoes are usually an exact fit. So I wouldn’t suggest going higher than one size above.

Finally, be aware that there are boys dress shoes that are casual and ones that are more formal. You will want to be sure to buy the proper dress shoes, based upon when they will be worn, and the durability of the shoe. As an example, a casual dress shoe for school can take an everyday beating, while a pair of oxford dress shoes should only be worn for special occasions.