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The Best Dress Shoes for Toddler Boys – Let me Show you the Most Popular and Versatile Style!

Sperry Top Siders For Toddlers

Have you been looking for the perfect pair of dress shoes for your toddler? Are you looking for a style that your toddler can wear for dress up occasions and at the same time be able to run and play comfortably?

I have been working at a specialized children’s shoe store for over 10 years now, and I handle approximately two hundred shoe fittings and try-ons per week. I have fitted hundreds of children’s shoes, and I am familiar with which shoe brands and which shoe styles are better than others.

For the last three years, I have been helping parents find the perfect pair of shoes for their kids ONLINE.

There is one particular dress shoe style for toddlers that I have found to be the most versatile one in terms of FIT (it will fit children with medium, wide, and extra wide feet), style (parents love how adorable this shoe style looks), and support (the shoe style comes with a rubber supportive sole, so your child can run around comfortably).

This is the most popular and versatile style because its a combination of FIT, STYLE, and SUPPORT.

Before presenting you with the best dress shoe style for toddler boys, I want to make sure that you know your child’s exact foot size. I always recommend parents to take their children to be properly fitted for shoes at their local children’s shoe store that they TRUST, where a shoe fitter can properly measure their feet. But if you are one of those parents without a shoe store in your area, please refer to an article I wrote called:

How To Measure Kids Shoe Size From Home – In Less Than 30 Seconds!

Are you familiar with the shoe styles called Sperry Topsiders? This is how they look like:

Sperry Boys Shoes

This dress shoe style that I recommend for toddlers resembles the exact same look, but it comes with Velcro closure, so you don’t have to worry about your toddlers’ shoes coming untie all the time. This is how the shoe styles looks:

Sperry Top Sider For Toddlers

Sperry For Toddlers

Pretty cool right?

Now let’s take a closer look at all the features this shoe style will provide for your child:

  • Leather upper: This shoe style is made of 100% genuine leather upper, which makes the shoe durable and breathable. Leather also allows the shoe to mold to the shape of your kids’ feet.

Sperry For Toddlers

  • Lightweight and Flexible: While this shoe style is supportive, it’s lightweight and flexible at the same time. This is a very important feature since it will prevent your toddler’s feet and legs from easily getting tired.

Dress Shoe For Toddlers

  • Easy On & Off: Parents love how easily these shoes are to put on and it gives children the independence of putting the shoes on and take them off by themselves.

Sperry For Toddlers

  • Memory Foam Footbed: The shoe style will come with a cushy memory foam footbed that will provide your child with all day comfort.

Kids Shoes With Memory Foam

This is the most popular dress shoe style for toddlers’ boys that I have fitted before. Parents keep coming back for the same shoe style since they love how versatile it is.

While I am in no sense a fashion expert, several parents have told me that his shoe style works well with any outfit.

Please keep in mind that this shoe style will fit a child with medium, wide, or extra wide feet, but it WON’T fit a child with narrow feet.

The Best Dress Shoes for Toddler Boys – The Secret Revealed!

This shoe style is available in two different colors. Here you can find this shoe style for the best price offered at Amazon:

Sperry Top Siders For Toddlers

Dress Shoe For Boy

This shoe style fits “short”, which means that you need to provide your child with a whole size longer of the size that he or she measured at the standard foot measuring tool (Brannock device), in order to allow for growing room. Keep in mind that this shoe will fit your child with wide or extra wide feet since it’s available in wide widths!

 Socks or No Socks with this Shoe Style?

I strongly recommend toddlers to wear socks with their shoes.  Socks act as a barrier between our kids’ feet and the shoes and prevent the formation and buildup of bacteria inside the shoes.

Socks will also cushion your kids’ feet and prevent the shoes from rubbing against your kids’ feet (this can lead to blisters).

While I can’t get into too much detail about the importance of wearing socks in this article, I wrote another post where I describe the best socks for kids, and you can find it here:

Seamless Socks For Kids – Stop The Struggle Of Putting Socks On!

The socks that I describe in that article are seamless and breathable!

Let’s see What Other Parents are Saying About this Shoe Style!

Perfect for my little guy ✅

I love these shoes! My son usually only wears tennis shoes but I needed to get him nicer shoes for a special occasion. He wore them for 8 hours straight and didn’t complain at all. I love the way they look and it’s so convenient that they are Velcro instead of shoelaces, so they are easy to put on and you can’t see the Velcro which makes them even more stylish!

I have been using them more often now that I know that my boy is comfortable in them.  I also love that they are available in wide widths since my child has wide feet and can’t fit in any shoes.

Fits wide or extra wide feet  ✅

The hidden Velcro on these is genius! Looks like a nice tied shoe without the struggle of having to tie our kids’ shoes. The leather and sole are both made of high-quality materials. My son wore these once a week until he outgrew them, and they still look like new. They hold up extremely well because they are made of leather.

This shoe fits kids with extra wide feet as well since I tested on my son, make sure you choose the W option.

Stylish velcro shoes that hold up ✅

This is the best shoe style that I have put on my baby. They match just about everything and stay on his feet. We get so many compliments on these. I will definitely be buying the next size up as soon as he outgrows them!

Have you tried this shoe style before? Do you have another dress shoe style that you recommend for children? Please share your thoughts and experiences below so others parents can benefit from them!


I created this webpage to help parents understand the importance that shoes have in healthy foot development and how they can prevent foot problems in the future.Join the rest of the parents who are taking care of their kid’s feet and get my guide for free: 10 Mistakes Parents Must Avoid When Buying Shoes for their Kids.

Join the rest of the parents who are taking care of their kids’ feet and get my guide for free: The 5 Most Common Mistakes Parents Make when Buying Their Kids’ Shoes

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