Whether it’s for work or your daily routine, many men today find themselves covering significant distances while sporting their dress shoes. This can quickly turn into a challenging endeavor, especially when traditional dress shoes tend to dish out a fair share of foot pain.

If not addressed, this discomfort can escalate into more serious foot issues. In the worst cases, medical and surgical intervention may be required.

The good news is that change is underway. Leading shoe manufacturers have caught wind of the evolving demands of the modern man. They’ve realized that comfort and style should go hand in hand.

As a result, contemporary dress shoe designs are integrating features that prioritize the foot health of professionals.

In this guide, we delve into the world of men’s dress shoes that are designed for walking. We’ll uncover what makes them so comfortable and provide you with guidance on what to look for when you’re out shopping for your own pair.

Lastly, we’ve put together a list of our top picks for dress shoes that are not only stylish but also well-suited for walking. You can easily purchase them online and experience the blend of fashion and comfort for yourself.

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What Are The Best Men’s Dress Shoes For Walking?

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Can Dress Shoes Be Made For Walking?

While it may seem counterintuitive, there are indeed dress shoes designed to provide maximum comfort and support for walking.

Traditionally, dress shoes were not primarily designed with walking (or extreme comfort, for that matter) in mind. However, modern brands have recognized the need for stylish yet comfortable options, especially for those professionals who find themselves walking many miles each day.

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In recent years, much progress has been made in the science of footwear. This has made it evident that dress shoes hardly catered to the health of our feet. Such attitudes led to countless professionals walking in uncomfortable dress shoes for decades.

There’s no question that most would opt for a pair of sneakers in the office, but the workplace dress codes that allow such casual footwear this are few and far between. This presents a challenge for those who need to look sharp while walking significant distances during their workday.

Consider this scenario: If your profession requires you to cover substantial distances within a single office space, such as moving between departments, navigating corridors, or climbing stairs, you’re essentially walking miles daily. Wearing conventional, uncomfortable dress shoes in such situations can lead to discomfort, foot pain, and potentially conditions like Plantar Fasciitis.

Investing in formal footwear designed for comfort and walking can make a significant difference in your daily life, enhancing both style and well-being.

Essential Features of Dress Shoes for Walking Comfort

Well Dressed Man In James L Fox Cigar ShopBrands like Wolf & Shepherd and Amberack (both featured below) have revolutionized the design of dress shoes, drawing inspiration from athletic footwear to cater to the needs of individuals who require both style and comfort during extended periods of walking.

However, even traditionally constructed dress shoes can offer features that greatly enhance your daily comfort and foot health.

When shopping for dress shoes suitable for walking, consider the following essential features:

  • Breathable Materials: Many synthetic leather materials don’t breathe and can cause the build-up of perspiration and heat, which is a breeding ground for blisters and bacteria. Opt for real leather, which acts as a membrane and reduces sweat.
  • Stability: Vital when walking, stable shoes ensure that you don’t have an unnatural stride, which can cause disorders and foot pain.
  • Cushioning: A characteristic of athletic footwear, which is becoming more common in dress shoes. Cushioning offers comfort to the contours of your feet to prevent aches and pains.
  • Shock Absorption: Until recently, the only shock absorption you could get was through rubber soles. Whilst good quality rubber does help, you can now find shoes with PU footbeds or EVA foam heels, which reduces the strain on your feet when walking.
  • Thicker Soles: Similar to shock absorption, thicker soles and lower heels offer a slight bounce and prevent all the weight moving towards the balls of your feet. Thin soles can be particularly painful after a long day spent walking.
  • Arch Support: Another characteristic of athletic footwear, arch support reduces pressure off the inner part of the bottom of your feet. This prevents the onset of Plantar Fasciitis. However, too much can cause bruising, so make sure it matches your foot shape.
  • Ankle Grip: Ankle notches or collars lock your feet in the shoe and stop them slipping out. This reduces friction and the chances of your developing painful blisters.

Which Dress Shoe Styles Are Best?

When it comes to choosing dress shoes that are best suited for walking long distances, it’s important to note that comfort isn’t solely determined by the shoe’s type. For instance, any loafer is not necessarily more comfortable than any oxford.

Man Walking in Suit And Dress Shoes

Regardless of the dress shoe style you choose, paying attention to specific comfort features such as cushioning, arch support, and breathable materials can significantly enhance your walking experience. The key is to strike a balance between style and functionality, ensuring that your dress shoes not only look great but also provide the comfort needed for extended periods on your feet.

Below, we present our top picks of the best men’s walking dress shoes. You’ll note how varied their designs are, yet all achieve the same goal – helping you rack up the miles every day and avoiding debilitating foot pain at the same time.

When you browse the list of dress shoes that we present below, you’ll quickly recognize that what makes a dress shoe comfortable is not its type.

The Best Men’s Dress Shoes For Walking

1. Wolverine 1000 Mile Boot [Dress Boots]

Wolverine Original 1000 Mile Cordovan Boot
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Overview

The aptly named 1000-Mile boots by Wolverine are a perfect formal alternative to regular dress shoes. As they’re boots, they offer more stability and support and you’ll also benefit from their comfort-oriented construction for walking.

How To Wear

In the review linked below, you’ll learn just how versatile these boots are to wear. Whether your needs are casual or formal, they will fit into most dress codes with the exception of perhaps the most conservative environments.

Best Colors

We love the Cordovan No.8 colour. However, you can also buy them in black or other various shades of brown. The Cordovan colour is the most versatile but if you have formal requirements, the black may be the ideal boot for you.

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2. Wolf & Shepherd Crossover Shoes [Comfortable Oxford]

Wolf & Shepherd CrossOver Longwing in Brown Leather
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Overview

Longwings are a popular type of dress shoe that usually encounter with much more noticeable ornamentation. However, Wolf & Shepherd has decided to keep the upper of their Crossover Longwings rather sterile to maintain a formal appeal.

Additionally, Wolf & Shepherd surpass their peers with patented comfort technology designed for professional men who are constantly on their feet. Features including a memory foam footbed and EVA foam heel render these a pleasure to wear.

How To Wear

Less formal than Oxfords, these Longwings are nevertheless very dressy. Were it not for the contrast sole (which ensures comfort while walking for extended periods), you could even get away with wearing the black leather version with a black tie ensemble.

The fact is that W&S wanted to create a modern version of the classic dress shoe, and this Longwing is easily one of the best within their Crossover collection.

Best Colors

Available in various tones of brown as well as in suede, you have plenty of options when it comes to picking the color that is best suited for your circumstances or particular workplace dress code.

3. Beckett Simonon Durant [Versatile Brogue]

Beckett Simonon Durant Quarter Brogue Shoe
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Overview

We were impressed by Beckett Simonon’s sheer quality given their relatively low cost. With Argentinian calfskin uppers that are handmade with a Blake stitch construction, they offer both durability and quality as well as comfort underfoot.

How To Wear

Perfect for a variety of dress codes, you could potentially wear these dressy Brogues everywhere. They’re great with jeans, chinos and even a tweed business suit. Whether your needs are casual, business casual or indeed professional, these are the perfect companion when always walking.

Best Colors

We’re quite fond of the tan leather. However, they’re also available in either Bordeaux or black, which adds some great variety when choosing. Given that the broguing details are quite subtle, these are one of the rare brogues that we’d say would look great in this color, too.

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4. Rockport Bryant Wing Tip [Affordable Brogue]

Rockport Bryant Wing Tip Walking Dress Shoes
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Overview

The final brogues in this list are more affordable but also designed with orthopedics in mind. An orthotic shoe, these Rockport Brogue Wingtips are designed to reduce pressure on the feet. Therefore, you’ll benefit from the proprietary TruTECH footbed which offers stability and cushioning when walking for extended periods.

How To Wear

We think these are great for business professional wear with a classic-cut suit. Accordingly, they’ll also shine in business casual settings with more creative suits.

Best Colors

For the most formal occasions, the black leather option is the one you’ll want to go for. However, the tan color will be more versatile and fit into more ensembles.

5. ECCO Citytray Plain Toe Tie [Derby Shoes]

ECCO Citytray Plain Toe Tie Dress Shoes For Men
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Overview

Ecco are renowned for making very comfortable shoes for the workplace. The Citytray Plain Toe Derby shoe is no different and features both the Fluidform comfort technology in the midsole and Tray technology in the outsole for increased grip and stability when walking.

Moreover, the upper is crafted from gold-rated full-grain leather that is supple and rich in color. Coupled with the comfort and support characteristics, these Ecco derbies are some of the best dress shoes you’ll find at this $200 price point.

How To Wear

Derby shoes are ideal if your dress code requirements are somewhere in the middle of the road. The design is relaxed enough for business casual wear but is also perfectly acceptable for more formal professional occasions.

Best Colors

Usually we’d refrain from wearing black derby shoes as the style is usually better with brown leather. However, if your professional needs require black shoes, we’d condone it. Otherwise, we’d have a preference for the brown leather, which has a slight burgundy allure to it.

6. Vionic Lucas [Dress Sneakers]

Vionic Lucas Dress Walking Sneakers
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Overview

Just a few years ago, it’d have been considered heresy to call a pair of sneakers a type of dress shoe. However, times are changing, trends are evolving, and many workplaces now permit polished pairs of sneakers to be worn without admonition.

Accordingly, we’ve specifically selected the Vionic Lucas sneakers as they epitomize the perfect fusion of style and comfort. Crafted with a sleek leather upper, they ensure a snug yet breathable fit. Moreover, the lace-up closure and round toe provide both style and convenience, while the pull tab on the collar adds an extra touch of functionality.

Finally, the Lucas sneakers feature Vionic’s innovative podiatrist-designed technology that offers superior orthotic support, relief, and stability.

How To Wear

When it comes to styling the Vionic Lucas sneakers, their versatility shines. While they may be sneakers, their polished look allows them to complement a range of outfits.

For a smart yet relaxed office ensemble, pair them with formal trousers or classic chinos. To embrace a more formal look, consider wearing them with well-fitted dress pants and a crisp button-down shirt.

Best Colors

When aiming for a more formal aesthetic, you’ll want to stick with the black leather option pictured above. The chocolate, light grey, olive, and pure white are also great varieties, but keep in mind that they’re the least formal.

7. Amberjack The Chelsea [Chelsea Boot]

Amberjack Brown Chelsea Walking Boots
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Overview

When it comes to boots that can be worn formally, few styles are better than the Chelsea boot. However, many Chelseas tend to be very narrow with unforgiving soles; Amberjack has changed all of this.

Aside from the beautiful and pliable leather upper, Amberjack’s The Chelsea also employs the brand’s unique sole technology. This includes a memory foam insole and dual-density outsoles that provide shock absorption and retain efficient traction.

How To Wear

These Chelsea boots are incredibly versatile and will fit in just about anywhere except for black tie events. Pair them with jeans or chinos when out on the town, or with a nice pair of trousers when in the office.

Best Colors

If you take a look at Amberjack’s website, you’ll see that these Chelseas are offered in 9 different versions, all of which are exceptional. Stick to the smooth leather varieties, and particularly the all-black Obsidian for the most formal settings. If you want a more versatile pair, then the Italian suedes are for you.

What Next?

Now that you have read about the best men’s dress shoes for walking, consider checking out some of our other related guides.

"Great for on the go. My job requires me to dress well but be on the move so these were perfect!."
Bespoke Unit Rating: ★★★★★

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