Dress shoes are an essential part of any man’s wardrobe. They are the final touch that can take an outfit from casual to formal, and they are often the first thing people notice about a man’s style. However, finding the perfect pair of dress shoes can be a challenge, especially if you have wide feet or a wide toe box. That’s why we’ve put together a list of the 5 best men’s wide toe box dress shoes plus a bonus shoe we think you’ll like.

When it comes to dress shoes, there are a few critical things to keep in mind. First and foremost, they need to be comfortable. You’ll likely be wearing them for extended periods, so you don’t want to be in pain or discomfort. Second, they need to be stylish. Dress shoes are often a statement piece, and you want to make sure they match your personal style and the occasion you’re wearing them for. Finally, they need to fit well. This is especially true if you have wide feet or a wide toe box. A poorly fitting shoe can cause blisters, discomfort, and even long-term foot problems.

With these factors in mind, we’ve scoured the market to find the 5 best men’s wide toe box dress shoes. We’ve tested each pair for comfort, style, and fit, and we’re confident that these shoes will meet your needs and exceed your expectations. So whether you’re dressing up for a wedding, a job interview, or a night out on the town, we’ve got you covered.

Best Men’s Wide Toe Box Dress Shoes

We understand that finding a comfortable pair of dress shoes can be a challenge, especially if you have wider feet or need a roomier toe box. That’s why we’ve done the research and compiled a list of the 5 best men’s wide toe box dress shoes based on 2023 sales data. Our selection includes shoes that are not only stylish but also provide the comfort and support you need to get through a long day at the office or a formal event. Check out our top picks below.

Dr Comfort Men's Dress Shoe | Wing

A timeless wide-width dress shoe with a modern twist by Dr. Comfort®! Crafted from high-quality full-grain leather.

CHECK PRICE

Pros:

• Comfortable and supportive: Full-grain leather upper, padded heel, and roomy toe box provide all-day comfort. Removable insoles allow for personalization and accommodate orthotics.
• Stylish and versatile: Classic wingtip design suits formal occasions and business casual settings.
• Durable: High-quality leather and hand-burnished finish ensure long-lasting wear.
• Supportive features: Wide toe box, lightweight outsole, and firm heel counter offer stability and shock absorption.

Cons:

• Break-in period: Leather shoes might require some time to break in for optimal comfort.
• Not as sleek as some dress shoes: The wingtip design and padded collar might not appeal to those who prefer a slimmer, more minimalist look.

Color:

Black, Chestnut

Size:

6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13, 14, 15

Width:

D, 2E, 4E

If you’re looking for a timeless dress shoe that’s both durable and stylish, the Dr. Comfort Wing Men’s Therapeutic Diabetic Extra Depth Dress Shoe is a great option. Here are the pros and cons of this product:

Pros

• The full-grain leather is durable and helps prevent skin irritation.
• The removable insoles can accommodate custom orthotics.
• The protective toe box provides extra protection from toe stubbing.

Cons

• Some users may find the shoe to be too narrow.
• The shoe may not be suitable for those with very wide feet.
• The shoe may be too expensive for some users.

Crafted from high-quality full-grain leather with a hand-burnished finish, the Dr. Comfort Wing Men’s Therapeutic Diabetic Extra Depth Dress Shoe is a top-quality shoe that helps prevent wear and tear. The protective toe box and padded heel provide extra comfort, while the removable insoles can be replaced with your own custom orthotics.

The lace-up design of the shoe ensures a precise fit, while the firm heel counter offers extra support and stability for daily activities. Whether you’re attending a formal occasion or a weekend gathering, the Dr. Comfort Wing dress shoe is a versatile option that can elevate your style.

Overall, we highly recommend the Dr. Comfort Wing  for those looking for a durable and stylish dress shoe that provides comfort and support.

Men's Plain Toe Suede Shoe | Finn

Inspired by the Chukka boot, the Finn by Propet is a men’s plain-toe suede shoe with detailed stitching that blends function and style.

FREE Gift with purchase - one set of our custom heat moldable inserts. An $80.00 value includes FREE.

CHECK PRICE

Pros:

• Comfortable: The soft suede or leather upper, cushioned insole, and removable orthotic insole make these shoes comfortable for all-day wear.
• Stylish: The classic oxford design is versatile and can be dressed up or down.
• Affordable: The Finn is a good value for the price.

Cons:

• Not as breathable as some other materials: The suede or leather upper may not be as breathable as some other materials, such as mesh.
• Less formal: While versatile, the classic oxford design isn't as formal as some other dress shoe styles like derbys or loafers, depending on the specific occasion.
• Maintenance requirements: Leather and suede uppers require regular cleaning and care to maintain their look and performance, which may be an inconvenience for some.

Color:

Black, Desert Camel, Stone, Tan

Size:

8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13, 14, 15

Width:

D, E, 3E, 5E

If you’re looking for a comfortable and stylish pair of dress shoes with a wide toe box, the Propét Men’s Finn Oxford is a great option. Available in both black and brown leather.

Pros

• The suede material gives these shoes a sophisticated look that pairs well with dress pants or chinos.
• The rubber sole provides excellent traction, making these shoes suitable for any weather condition.
• The high-density open-cell foam keeps your feet cool and comfortable all day long.

Cons

• Some customers have reported that the shoes run a bit large, so you may need to order a half size down.
• The shoes may not be suitable for people with high foot arches, as they may not fit well.
• Some customers have reported issues with the quality and durability of these shoes.

These shoes are perfect for any occasion, whether you’re attending a wedding or going to work. The suede material gives them a timeless look that will never go out of style. The rubber sole provides excellent traction, making them suitable for any weather condition.

The high-density open-cell foam is a standout feature of these shoes. It allows air to circulate, keeping your feet cool and comfortable all day long. The EVA spacer also allows you to customize the fit to your liking.

Overall, the Propét Men’s Finn is a great option for anyone looking for a comfortable and stylish pair of dress shoes with a wide toe box.

Men's Dress Leather Boot | Astute by Pilgrim

These men's comfortable and stylish dress boots, Astute by Pilgrim, are ready for business meetings or dinner with clients.

CHECK PRICE

Pros:

• Comfortable: The cushioned footbed, flexible construction, and supportive features make these shoes comfortable for long periods of wear.
• Stylish: The classic design and high-quality materials make these shoes suitable for formal occasions.
• Durable: The leather upper and durable outsole ensure long-lasting wear.
• Supportive: The fiberglass shank and dual-density midsole provide arch support and stability.
• Accommodates orthotics: The removable footbed allows for customization with orthotics if needed.

Cons:

• Limited breathability: Leather uppers can trap heat and moisture versus mesh uppers.
• Potentially less flexible: Some users report the fiberglass shank can limit flex compared to shoes without it.
• Break-in period: Leather shoes may require some time to break in for optimal comfort.

Color:

Black

Size:

7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13

Width:

D, 2E, 4E

If you’re looking for comfortable and stylish dress boots, Pilgrim Men’s Dress Boots are an excellent choice. We highly recommend these boots to anyone who wants to look good and feel comfortable at the same time.

Pros

• Lightweight and well-ventilated
• Removable cushioned open-cell PU insole
• Flexible dual-density EVA cradles the foot for enhanced comfort and support

Cons

• Not suitable for heavy-duty work
• Limited color options
• May not fit all foot shapes

The Pilgrim Men’s Dress Boots are incredibly comfortable, thanks to the stretchable leather upper, padded collar and tongue, and microfiber lining. The removable cushioned open-cell PU insole provides extra support and comfort, and the flexible dual-density EVA cradles the foot for enhanced comfort and support.

These boots are also extra lightweight, making them perfect for all-day wear. The contoured orthotic insole, with anatomical arch support and gel-padded heel seat, helps alleviate foot pain and enhances comfort from heel to toe. The heel cradle system provides extra support and stability, and the toe box height is 1-1/8″ with removable inserts.

The Pilgrim Men’s Dress boots are diabetic approved footwear, and the strobel construction and contoured last bottom allow for flexibility and extra comfort. The reinforced heel counter and extra strength in the midsection eliminate added wear and tears to your feet.

For those looking for comfortable and stylish dress boots, the Pilgrim Men’s Dress Boots are an excellent choice. They’re lightweight, well-ventilated, and provide extra support and comfort, making them perfect for all-day wear.

Pilgrim Men’s Dress Shoe Richard

Men's Dress Shoe | Richard by Pilgrim

Stylish and comfortable men's dress shoe with Velcro strap for easy access - the Richard by Pilgrim Shoes.

CHECK PRICE

Pros:

• Comfortable and stylish: The full-grain leather upper and removable insole offer comfort and breathability, while the classic design makes it suitable for various dressy occasions.
• Supportive features: The hook and loop closure, Strobel construction, and contoured last provide good support and stability.
• Diabetic-friendly: The wider toe box, seamless lining, and diabetic-friendly outsole cater to individuals with foot concerns due to diabetes.

Cons:

• May not be ideal for all-day wear: The dress shoe design might not be suitable for extended periods of standing or walking, especially for those with demanding jobs or activities.
• Hook and loop closure may not be as secure as laces: While convenient, the hook and loop closure might not provide the same level of secure fit as traditional laces for some individuals.

Color:

Black, Brown

Size:

7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13

Width:

D, 2E, 4E

This versatile shoe is designed to elevate your everyday wardrobe while prioritizing your foot health. Here’s what makes it special:

Pros:

• Comfortable and stylish: The full-grain leather upper and removable insole offer comfort and breathability, while the classic design makes it suitable for various dressy occasions.
• Supportive features: The hook and loop closure, Strobel construction, and contoured last provide good support and stability.
• Diabetic-friendly: The wider toe box, seamless lining, and diabetic-friendly outsole cater to individuals with foot concerns due to diabetes.
• Multiple sizes and widths: Ensures a perfect fit for various foot shapes and needs up to 4E in mens.

Cons:

• May not be ideal for all-day wear: The dress shoe design might not be suitable for extended periods of standing or walking, especially for those with demanding jobs or activities.
• Hook and loop closure may not be as secure as laces: While convenient, the hook and loop closure might not provide the same level of secure fit as traditional laces for some individuals.

Ultimately, the pros and cons of the Pilgrim Shoes Richard depend on your individual needs and preferences. If you’re looking for a comfortable and stylish dress shoe for occasional wear, this is a great option. However, if you need a shoe for all-day comfort, that requires hours of standing, you might want to consider a more robust option.

The Pilgrim Richard is a great choice for men seeking a comfortable and stylish dress shoe. Its versatile design, supportive features, and the diabetic-friendly build make it suitable for various needs business styles and preferences.

Men's Comfort Shoe | Orthofeet Broadway

The Orthofeet Broadway men's comfort shoe is a trusted companion for daily urban adventures. delivering a potent blend of support and comfort

*FREE Gift with purchase - one set of our custom heat moldable inserts. An $80.00 value!

CHECK PRICE

Pros:

• Comfortable and supportive: The cushioning, leather upper, and deep toe box make these shoes comfortable for walking and standing for extended periods.
• Accommodates foot conditions: The extra depth, removable inserts, and wide toe box make these shoes suitable for people with diabetes, bunions, hammertoes, and swelling.
• Adjustable: The easy-closure strap allows for a customized fit.
• Durable: The leather upper and sturdy construction ensure long-lasting wear.
• Multiple widths: Available in medium, wide, and extra-wide to accommodate different foot shapes.

Cons:

• Bulkier design: The extra depth and width may make these shoes feel heavier and less flexible than other convential shoes.
• Limited breathability: The leather upper may not be as breathable as mesh or other materials.

Color:

Black

Size:

7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13, 14, 15

Width:

B, D, 2E, 4E, 6E

These shoes are perfect for anyone looking for comfort and foot support. With Orthofeet Ortho-Cushion technology, you can say goodbye to foot and heel pain and hello to happy feet. The Broadway shoes are designed with premium orthotic insoles, anatomical arch support, and Arch Booster technology to re-align your feet and improve your posture. The wide toe box alleviates pressure on swollen feet, bunions, and hammertoes.

Pros

• The Ortho-Step insole provides support and accommodates orthotics.
• The flexible, non-binding collar enhances comfort and protects your feet.
• The lightweight outsole absorbs impact without adding weight to your step.

Cons

• The velcro strap may wear out over time.
• The shoes may not be suitable for those with very narrow feet.
• The leather may require regular maintenance to keep it looking good.

These shoes are incredibly comfortable and provide excellent support for your feet. The Ortho-Step insole is especially helpful for those with orthotics, as it provides additional support and cushioning. The flexible, non-binding collar is also a great feature, as it ensures that the shoes are comfortable to wear for extended periods.

The lightweight outsole is another great feature, as it absorbs impact without adding weight to your step. This makes walking easier and more comfortable, especially for those who spend a lot of time on their feet. The only downside is that the velcro strap may wear out over time, but this is a minor issue compared to the overall comfort and support provided by these shoes.

In conclusion, if you’re looking for a comfortable and supportive shoe that can alleviate foot and heel pain, the Orthofeet Broadway shoes are an excellent choice. They’re perfect for anyone who spends a lot of time on their feet, and they’re especially helpful for those with orthotics.

Bonus Shoe

Dress Shoe For Men | Dr Comfort Classic

The Dr. Comfort Classic men's dress shoe redefines the traditional men’s dress shoe with a blend of sophisticated craftsmanship and modern engineering, making it suitable for both formal and informal occasions.

CHECK PRICE

Pros:

• Comfortable and supportive: The cushioned footbed, supportive features, and wide toe box make these shoes comfortable for extended periods on your feet.
• Stylish: The classic dress shoe design with hand-burnished leather ensures a sophisticated look.
• Durable: The high-quality leather and construction ensure long-lasting wear.
• Customizable: The removable footbed allows for personalization and the use of orthotics if needed.

Cons:

• Limited breathability: Leather uppers might trap heat and moisture.
• Break-in period: Leather shoes might require some time to break in for optimal comfort.

Color:

Black, Chestnut

Size:

6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13, 14, 15

Width:

D, 2E, 4E

If you’re looking for a comfortable dress shoe that can accommodate your orthotics, then the Dr. Comfort Classic Men’s Therapeutic Dress Shoe in black or brown is a great option.

Pros

• The high-polished, hand-burnished leather with detailed stitching creates a clean and simple design that exudes sophistication.
• The soft, cushioned leather and padded tongue and heel cuff provide all-day comfort.
• The removable footbeds can accommodate your orthotics, ensuring that you can wear your own insoles without any discomfort.

Cons

• The price of these shoes is on the higher side.
• The shoes may not be as durable as some other dress shoes.
• The shoes may not be suitable for those with very wide feet.

The Classic by Dr. Comfort® is a reinvented traditional dress shoe that combines sophisticated craftsmanship with modern engineering. The shoe features a protective toe box that provides extra protection from toe stubbing, and the top-quality material and construction ensure durability. The firm heel counter provides support and stability for everyday wear, while the lightweight outsole with a skid-resistant finish makes the shoe perfect for work or any formal occasion.

The shoes are made of 100% leather, which is a natural material that helps regulate heat and keep feet cool and dry. The leather sole adds to the overall durability of the shoe, and the use of top-quality material and construction helps prevent wear and tear.

The Dr. Comfort Classic dress shoe is a great option if you’re looking for a classic dress shoe that can accommodate your orthotics. The shoes are made of high-quality materials and construction, and the design is both sophisticated and simple.

Buying Guide

When choosing the best men’s wide toe box dress shoes, there are several features to consider to ensure comfort and style.

• Toe Box Width: The most important feature to consider is the width of the toe box. A wider toe box allows for more room for your toes to move around, reducing the risk of blisters and discomfort. Look for shoes that are specifically designed for wide feet or have a wider toe box.
• Material: The material of the shoe can also affect its comfort and durability. Leather is a popular choice for dress shoes as it is durable and breathable, allowing your feet to stay cool and dry. However, synthetic materials can also be comfortable and durable, so choose the material that best suits your needs and preferences.
• Cushioning and Arch Support: Cushioning and arch support are also important features to consider when choosing a dress shoe. Look for shoes with a cushioned insole and arch support to reduce the risk of foot pain and discomfort.
• Style: While comfort is important, style is also a key factor in choosing dress shoes. Look for shoes that match your personal style and can be worn with a variety of outfits. Classic styles such as oxfords, loafers, and brogues are versatile and timeless options.
• Sizing: Finally, it’s important to ensure that you choose the correct size. Measure your feet and refer to the manufacturer’s size chart to find the best fit. Keep in mind that different brands may have different sizing, so it’s important to try on shoes before purchasing if possible.

Have Questions?

Reach out and contact a DT Footwear fit specialist for personalized assistance via phone, email or text. Our fitment experts are here to guide you towards achieving Happy Feet. With a variety of footwear options available, stepping into comfort and style has never been easier.

The DT Footwear Guarantee

Free shipping

We offer free shipping anywhere in the U.S.
Quick delivery from 10 US warehouses

Sizing Questions

Need help with sizing? Call, email, or text to speak to our Fitment Specialists.

BONUS Inserts

Receive up to 3 free BONUS inserts per shoe with your purchase. (Not available with all styles)

SHOP NOW

Disclaimer: Educational Information Only

The information provided here is for educational purposes only. It is not a substitute for professional medical advice or treatment, including any foot-related concerns. If you have any health issues or questions about your feet, please consult a qualified healthcare professional, like a doctor or podiatrist. Don’t ignore medical advice or delay seeking help based on what you read here or elsewhere. We’re not responsible for any harm caused by using this information. Everyone’s response to treatments can be different, and medical recommendations may change over time. If you experience a medical emergency or serious foot problem, seek immediate medical attention, or call your local emergency services. By using this resource, you agree to these terms and understand the importance of getting personalized medical advice from a qualified professional.