Best Dress Shoes for Kids with High Insteps – Stylish, Comfortable, and Extra Deep!

Finding dress shoes for kids with high insteps can feel nearly impossible—you’re not alone! I hear from countless parents who struggle to find a single pair of dress shoes that fit their child’s high instep comfortably. Since dress shoes are often designed with less flexibility and depth, the challenge becomes even greater. The good news? Based on my many years of experience as a shoe fitter, I’ve put together a curated list of the best dress shoes for kids with high insteps to help make your search a whole lot easier.

How Does a Foot with a High Instep Looks Like?

Before diving into shoe recommendations, it’s important to understand what a high instep is and how it affects shoe fitting. The instep is the top part of the foot, and a high instep means this area is more pronounced or elevated.

An image highlighting the instep of the foot, showing exactly where this important area is located to better understand how it affects shoe fit.
An additional helpful image pinpointing the instep on a child’s foot, making it easier to understand why this area plays a big role in finding the right shoe fit.

Children with high insteps often experience challenges such as tightness and pressure on the top of the foot. This can lead to discomfort, red marks, and in some cases, pinching or blisters. These children may also find it difficult to fit into standard shoe sizes, necessitating a more customized approach to shoe shopping.

What Makes the Dress Shoes I Recommend Effective for High Insteps?

When selecting dress shoes for children with high insteps, certain features can make a significant difference in comfort and fit.

1. Extra Depth: Extra depth in a shoe allows more room for the foot, which is particularly beneficial for accommodating a high instep. This feature can prevent the shoe from pressing down uncomfortably on the top of the foot.

See how the dress shoe on the right offers much more depth than the one on the left — a key difference for a better fit!

The same goes for girls’ dress shoes — especially the popular Mary Jane style that so many girls love to wear for special occasions and everyday dress-up!

Notice how the Mary Jane on the right offers much more depth than the one on the left.

2. Oversized Openings: Shoes with oversized openings make it easier to slide the foot in without forcing it into a tight space. This reduces the risk of discomfort and ensures a better fit.

An image of one of the dress shoes I recommend with double velcro straps for easy on and off.

3. Flexible Material and Adjustable Straps: Opt for shoes made from soft, flexible materials that can adapt to the shape of the foot. Adjustable straps or laces are also beneficial as they allow for custom fitting.

High Instep Struggles: Why Kids’ Dress Shoes Are Hard to Find

The main challenge in finding dress shoes for kids with high insteps is that shoes aren’t labeled as “extra deep,” so it’s tough to know if they provide the necessary depth unless you’ve tried them on before. That’s where my expertise comes in. With years of experience fitting kids’ shoes, I know which dress shoes offer more depth and better support for high insteps. But before I share my top picks, it’s important to make sure you know your child’s exact foot size to ensure a perfect fit.

How to Retrieve Your Child’s Exact Foot Length and Shape

Determining the correct shoe size can be tricky, especially when buying online. My virtual shoe fitting service can help you accurately measure your child’s feet and receive personalized recommendations tailored to your child’s instep height and exact foot shape.

Below you can find the best dress shoes for kids with high insteps that combine style, comfort, and the necessary features to support healthy foot development. Disclosure: Some links in this post are affiliate links, meaning we may earn a small commission at no extra cost to you.

Best Dress Shoes for High Instep – Stylish and Extra Deep

The dress shoes I recommend come in medium (M) and wide (W) widths, so be sure to choose the right fit for your child. If your child has a high instep, it’s very likely you’ll need the wide (W) option for the best comfort and support.

1. Berwyn by Florsheim

These dress shoes for high instep are available in wide widths, which makes them an excellent option if your child happens to have wide feet as well. Known for their quality craftsmanship, these shoes offer both style and comfort, making them perfect for formal occasions.

Black dress shoes for boys with wide feet.
  • Order the shoe Loafer Church by French Toast on Zappos or Amazon
  • Available in medium and wide widths
  • Padded tongue and collar provide additional comfort and cushioning
  • Genuine leather
  • I suggest that you get this shoe a whole size larger than your child’s current foot size

2. Allie Mary Jane by Footmates

These wide width Mary Jane shoes are a fantastic option for girls with wide feet and high insteps who love a classic look. The adjustable straps allow you to customize the fit and prevent putting excessive pressure on your child’s instep.

White Mary Jane for toddler girl with wide feet.
  • Order the shoe Allie Mary Jane by Footmates on Amazon or Zappos
  • Fits medium and wide feet
  • Easy on-and-off with an oversized opening hook and loop closure
  • Buckle closure for a secure and adjustable fit
  • I suggest that you get this shoe a whole size larger than your child’s current foot size

3. Murphy by Stride Rite

This classic dress shoe is a fantastic choice for children with high insteps as it provides ample room in the toe box and features a comfortable fit that supports your child’s foot shape. The classic design makes them suitable for a variety of settings.

Black dress shoes for boys with wide feet.
  • Order the shoe Murphy Sneaker by Stride Rite on Amazon or Zappos
  • Available in medium and wide widths
  • Lace-up closure
  • Premium leather with a padded heel collar
  • Memory-foam insole provides enhanced comfort 
  • I suggest that you get this dress shoe a whole size larger than your child’s current foot size

4. Shoe style Holly Mary Jane by Stride Rite

These deep and wide Mary Jane shoes for high instep are another stylish option. With its roomy toe box and supportive design, it’s an ideal choice for girls needing a bit more width in their shoes.

Stride Rite Holly Mary Jane in gold for girls.
  • Order the shoe Holly by Stride Rite on Zappos or Amazon.
  • Available in extra wide widths.
  • Awarded the Seal of Acceptance from the American Podiatric Medical Association (APMA).
  • Padded tongue and collar for added comfort.
  • Supreme comfort care of Ortholite memory foam footbeds.
  • I suggest that you get this Mary Jane shoe a whole size larger than your toddler’s current foot size.

5. Great Lakes by Florsheim

This dress shoe provides extra depth that helps accommodate high insteps and broader feet while maintaining a sleek, polished appearance. This shoe is a great option for special events and formal gatherings.

Narrow dress shoes for boys.
  • Order the shoe Great Lakes by Florsheim on Zappos or Amazon
  • Fit medium or wide feet
  • Leather and textile upper
  • Moisture-wicking lining
  • Lace-up closure
  • I suggest that you get this shoe half a size larger than your toddler’s current foot size

6. Bonnett by Nina

These black Mary Jane shoes provide a wide and deep fit and are a stylish option for girls. The elegant design makes them suitable for both casual and formal settings, allowing for versatility in a child’s wardrobe.

Key Features

  • Order the shoe Bonnett by Nina on Zappos or Amazon
  • Available in medium and wide widths
  • 100% leather
  • Padded collar
  • Cushioned soles
  • I suggest that you get this shoe half a size larger than your toddler’s current foot size

7. School Days by Keds

These high instep shoes are a versatile choice, suitable for both school and special occasions. Perfect for both boys and girls, providing a wider fit for everyday wear.

Narrow dress shoes for kids.
  • Order the shoe Bonnett by Nina on Amazon or Zappos
  • Available in medium and wide widths
  • Lace-up closure offers a snug fit for all-day wear
  • Padded collar
  • I suggest that you get this shoe half a size larger than your toddler’s current foot size

8. Mary Jane by FunkyMonkey

These wide fit high instep Mary Jane shoes offer a playful twist on the classic design. They come in a range of colors and patterns, allowing your child to express their individuality while enjoying a comfortable fit.

Red patent toddler Mary Jane dress shoe.
  • Order the shoe by FunkyMonkey on Amazon
  • Fits medium or wide feet
  • Velcro buckle secures the perfect fit every time
  • Lightly padded leather insoles
  • I suggest that you get this shoe a whole size larger than your child’s current foot size

9. Bogan Jr. by Florsheim

The Bogan Jr. by Florsheim is a great option for boys with high insteps. These shoes are available in actual wide widths in case your child has broader feet.

Black slip on dress shoes for kids with wide feet.
  • Order the shoe Soft Slip by Lonsoen on Amazon or Zappos
  • Available in medium and wide widths
  • Slip-on design
  • Made from soft PU leather material
  • I suggest that you get this shoe a half size larger than your child’s current foot size

10. Claire by Stride Rite

These extra wide Mary Jane shoes are available in wide and extra wide widths and the classic design makes them suitable for various occasions. Ideal for children with high insteps.

Extra wide Mary Jane shoe for toddler girls.
  • Order the shoe Claire by Stride Rite on Amazon
  • Available in medium, wide, and extra wide feet
  • Crafted from a premium leather upper
  • Padded collar
  • I suggest that you get this shoe a whole size larger than your child’s current foot size

11. Lonsoen Lowfur

These high instep shoes are an affordable option for parents looking for budget-friendly wide dress shoes. Despite their lower price point, they do not compromise on comfort or style.

Brown loafer for toddlers with wide feet.

Key Features

  • Order the shoe Soft Slip by Lonsoen on Amazon
  • Fits medium or wide feet
  • Padded tongue and collar provide additional comfort and cushioning
  • 100% synthetic 
  • I suggest that you get this shoe a half size larger than your child’s current foot size

12. Allie by Footmates

These deep and wide width Mary Jane shoes feature a leather upper that provides a classic look, while the cushioned footbed ensures all-day comfort.

Mary Jane dress shoe for toddler girls with wide feet.
  • Order the shoe Allie Mary Jane by Footmates on Amazon or Zappos
  • Fits medium or wide feet
  • Easy on-and-off with an oversized opening hook and loop closure
  • Rounded, slip-resistant soles encourage natural motion and help improve balance
  • I suggest that you get this shoe a whole size larger than your child’s current foot size

While these dress shoes are crafted from high-quality materials and offer great cushioning, it’s important to set the right expectations with your child: dress shoes will never feel as soft and flexible as sneakers. No matter how well-made, dress shoes are naturally stiffer — but that’s simply part of their design and purpose.

Contact Me for Personalized Recommendations

If you need specific shoe recommendations tailored to your child’s instep height and exact foot shape, feel free to contact me via email. As a passionate shoe fitter, I am dedicated to helping families find the best footwear solutions for their children’s needs. Through a personalized consultation, we can explore various options and find the perfect match for your child’s requirements. My goal is to make the shoe selection process as smooth and informed as possible, ensuring your child enjoys the benefits of well-fitted, comfortable footwear.

Additional Resources for Children with High Insteps

Finding the right dress shoes is just one part of the puzzle. Children with high insteps may also benefit from specific recommendations for seasonal shoes (sandals or boots) and everyday sneakers. These shoes should offer similar features such as extra depth and adjustability to ensure year-round comfort.

How to Tell When a Child Has a High Instep?

After years of experience, I can often spot a high instep just by looking at a child’s feet — but you can also identify it yourself with a few simple observations:

Shoe Fit: If you constantly struggle to get your child’s shoes on, that’s often the first clue that they might have a high instep.

An image of a child struggling to get her shoes on.

Pressure Marks: Red marks or indentations on the top of the foot after wearing shoes are another sign. These pressure marks can lead to sores or calluses if not addressed, making it crucial to choose shoes that accommodate this foot shape.

Indentations on the top part of your child’s feet are a clear sign sign that your child might have a high instep.

With my top recommendations and virtual shoe fitting service, you can confidently select shoes that are both stylish and functional. Remember, the right pair of shoes can make all the difference in your child’s foot development and overall comfort.