Whether it’s a question of work or lifestyle, men can find themselves walking long distances whilst wearing dress shoes. However, this can become extremely tiring as the wrong shoes can lead to injuries and disorders such as Plantar Fasciitis.
After testing dozens upon dozens of shoes, behold the ultimate list of the best men’s dress shoes for walking:
- Dress Boots: Wolverine 1000 Mile Cordovan
- Comfortable Brogue: Wolf & Shepherd Senna Wingtip
- Versatile Brogue: Beckett Simonon Durant Quarter Brogue
- Affordable Brogue: Rockport Almartin
- Derby Shoe: Ecco Lisbon Plain Toe Tie
- Chukka Boot: Vionic Chase
If there’s a pair listed above that have caught your eye, use the links to jump ahead. If not, scroll down to learn more about each. We’ll also talk about the best features in dress shoes that help make lots of walking more comfortable.
Quick Buyer’s Guide
Don’t have time to read about each shoe? Use the Quick Buy Guide to start shopping now! Alternatively, you can learn the details of the individual shoes by scrolling down.
Dress Boots
Comfortable Brogue
Brogue Shoe
Affordable Brogue
Derby Shoe
Chukka Boot
See All Bespoke Unit Dress Shoe Guides
Other Waking Shoe Guides
Recommended Shoe Guides
- Style: Derby / Bluchers
- Formality: Casual
- Pricing: $365 [Buy From Wolverine]
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.
Also Featured In
- Style: Blind Brogues
- Formality: Business Professional
- Pricing: $365 [Buy From Wolf & Shepherd]
Overview
Traditionally a rustic walking shoe, you’ll coincidentally see a number of brogues on this list. However, 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 still retain a measure of dressiness by being blind brogues. This means that there’s no toe medallion and so less ornamentation. However, they’re both dressy yet versatile for a number of different dress codes that you may encounter.
Best Colors
Available in honey tan, mid-brown maple or black, there are a few options to choose from according to your needs. However, should you need something much more formal, there’s also an Oxford shoe, which offers the same features.
Also Featured In
- Style: Brogues
- Formality: Business Casual
- Pricing: $199 [Buy From Beckett Simonon]
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’re 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 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 colour too.
Also Featured In
- Style: Brogues
- Formality: Business Professional
- Pricing: $119.95 [Buy Now On Zappos]
Overview
The final brogues in this list are more affordable but also designed with orthopaedics in mind. An orthotic shoe, they’re designed to reduce pressure on the feet. Therefore, expect features such as the EVA footbed, which offers stability and cushioning when standing or walking.
How To Wear
We think these are great for business professional wear with a classic-cut suit. However, you could probably push it all the way up to cocktail attire as they’re really rather stylish for orthotic shoes!
Best Colors
Something of a contrast to the Strandmoks above, the Almartin is only available in black. As such, they’re more understated, which makes them a better choice for formal wear.
Also Featured In
- Style: Derby Shoes
- Formality: Business Professional
- Pricing: $170 [Buy Now On Zappos]
Overview
Ecco are renowned for making very comfortable shoes for the workplace. The Lisbon derby shoe is no different and features the brand’s Comfort Fibre System, which makes them very satisfying for walking. Furthermore, the outsole is made from direct-injected PU, which provides both a lightweight fit and shock absorption.
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.
Also Featured In
- Style: Chukka Boots
- Formality: Business Casual
- Pricing: $160 [Buy Now On Zappos]
Overview
Vionic’s orthotic chukka boots are exceptional and indistinguishable from regular chukkas. We were very impressed by the comfort they offered thanks to the EVA footbed designed by podiatrists. Furthermore, they’re a supportive boot that’s great for all-year wear.
How To Wear
A very versatile example of footwear, chukka boots are great for wearing through-out the year. Whilst they’re on the more casual end of the scale, they can be worn in a number of situations and even paired with a more relaxed yet stylish suit.
Best Colors
Available in either tan or black, which are both made from water-resistant suede. We have a preference for the tan as these are much easier to wear in casual scenarios whilst the black can be a touch too dressy.
Also Featured In
Are Dress Shoes Made For Walking?
Although it may sound like an oxymoron, there are indeed dress shoes that are good for walking. While it’s not an activity that the shoes were originally designed to endure, brands have realised that there are certain contemporary needs to fulfil.
Indeed, a lot of progress has been made in the science of footwear and we’ve learned that dress shoes weren’t always catering to the health of our feet. Nevertheless, many professional men have worn dress shoes for decades at their workplace.
As such, there has been a growing tendency to dress down and wear more comfortable shoes for work. However, few people have this luxury. Furthermore, there is a growing resurgence in formal business attire as a style rather than an obligation.
Still, many of us have professions where we are required to walk miles everyday. This isn’t necessarily a question of walking from one place to another but usually consists of moving around a single space.
For instance, unless you’re using a step counter, you may not realise the miles that you may accrue in a single office space. Anyone who works in an environments with steps, corridors or different departments may cover serious distances while having to adhere to a dress code with formal shoes.
Therefore, if this sounds like you, consider investing in footwear that will make life easier rather than potentially bring about conditions like Plantar Fasciitis.
Dress Shoe Features For Walking
Brands like Wolf & Shepherd have completely rethought the way dress shoes are designed in order to cater to walking long distances. Rather than crafting a traditional dress shoe, they have sought inspiration from athletic footwear instead.
However, even classic dress shoes can have the odd feature, which can make a fundamental difference to your daily life. Consider seeking out shoes with some of the following 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.
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.
- Best Men’s Shoes For Work
- Most Comfortable Dress Shoes For Men
- Best Dress Shoes For Standing All Day
- Best Business Casual Shoes For Men
- All Men’s Dress Shoe Buying Guides
- Bespoke Unit Shoe Homepage
"Great for on the go. My job requires me to dress well but be on the move so these were perfect!"Rating: 5.0 ★★★★★
Shoe Content
Very effective and informative article which I want. I love this article very much. I broke my leg a few days back falling from the balcony. I hit my leg on a concrete statue and broke it. The balcony wasn’t too high, but Somehow I managed to break my leg. Now I am in total bed rest, my leg is cast and the doctor prescribed a walking shoes. Does it get sweaty inside the shoe, is it comfortable?
It shouldn’t really get sweaty, no. It really depends on the shoe and the socks that you wear! But if your leg is broken, can you even fit one over the cast?