One of the greatest advantages for men in donning dress boots is that extra level of comfort. Whilst there are indeed many very cosy dress boots out there, which are the most comfortable?

Therefore, this guide has been written in order to provide you with the definitive list of the best and Most Comfortable Dress Boots For Men that you can buy online:

  1. Wolf & Shepherd Breakaway Boot
  2. Ross & Snow Riccardo
  3. Idrese Custom Boots
  4. Allen Edmonds Sullivan
  5. Beckett Simonon Douglas Jodhpur Boot
  6. Ace Marks Hugo Boot
  7. Johnston & Murphy Forrester Shearling Boot
  8. Johnston & Murphy Copeland Chukka
  9. Taft Branson Boot
  10. Vionic Chase Chukka Boot

See something that you like? Use the links above to jump ahead or scroll down to see them all. We’ll also quickly cover the sort of boot features that tend to offer an extra level of comfort so you know what to look for.

Wolf & Shepherd Breakaway Boots On Box

wolf & shepherd banner

Beckett-Simonon-Ethical-Ad-2

What Are The Most Comfortable Dress Boots For Men?

Advert Title Text Banner Zappos Mobile Link Block Ad

Want To See More Dress Boot Guides?

Read Now

1. Wolf & Shepherd Breakaway [Blucher Boot]

Wolf & Shepherd Breakaway Boots Feature
Shop Now

By far the most comfortable dress boots that we’ve tested, the Breakaway boot from Wolf & Shepherd features an EVA heel for extra cushion. Meanwhile, the memory foam footbed cups the contours of the foot. Finally, the boots are very light thanks to their unique construction, which reduces fatigue.

Very versatile to wear, the Breakaway boots can be sported both casually and relatively formally. We’d wear them with a suit and jeans alike. However, this depends on the colour.

If you’re looking for a formal boot, the Onyx black calfskin leather would be the best choice. Meanwhile the reddish hue of the Cognac is quite versatile. Finally, the honey tan is a very casual option.

"Like walking on clouds, the Breakaway is specifically designed to merge style and comfort and offers a remarkably versatile boot."
Bespoke Unit Rating: ★★★★★

2. Ross & Snow Riccardo Blucher Boot

Ross & Snow Riccardo Boot
Shop Now

Reminiscent of classic Red Wings, Ross & Snow’s Riccardo is a cut above any winter boot that we’ve tried. They’re effortlessly stylish but feature sturdy construction and supple rustic-style leather.

The Italian calfskin leather uppers are lined with organically-raised and ethically-sourced shearling wool. As a result, they’re unbelievably warm and it’s sometimes tempting to live the on around the house.

Furthermore, the footbed is removable and you’ll have the choice between a shearling or a cushioned ergonomic insert for additional support. While the regular insert is nice, we can’t help but always wear it with shearling.

They’re admittedly pricey, but you’ll be hard-pressed to find a more comfortable and stylish boot. Although the Wolf & Shepherd does a fine job, we do think that they’re outperformed by the Riccardo.

3. Idrese Custom Shoes

Idrese Shoe Review
Shop Now

Goodyear-welted custom full-grain leather boots that you can design yourself for less than $300? Sounds too good to be true, doesn’t it? When Jawad Malik founded Idrese, his objective was to provide people with the opportunity to do just that.

You can create your own boots using Idrese’s online 3D designer, which are then crafted for you in Almansa, Spain. Traditional brogue boots are a tad more experience at $315. However, Jodhpur, Chelsea, and Chukka boots each retail for $295.

Idrese’s comfort resides primarily in its vast range of widths and sizes. Rather than have to settle for something that just about fits but may feel snug, Idrese caters to every foot size and shape.

4. Allen Edmonds Sullivan Street Blucher Boots

Allen Edmonds Sullivan Dress Boot
Shop Now

Another classic Blucher boot, the Allen Edmonds Sullivan Street is a specimen of traditional footwear like the Wolverines above. A Goodyear welt ensures longevity whilst the Dainite rubber soles provide traction and shock absorption.

With a combination of smooth and pebbled calfskin leather, these boots can be worn across a spectrum of dress codes. Furthermore, the balmoral cap toe offer an extra degree of formality so you can either choose to wear these with plain jeans or a three-piece business suit.

Although we tend to have a preference for brown leather boots, the black feels more effective in this scenario. Thanks to the features detailed above, they’re rendered more formal and usable for both business casual and professional wear.

5. Beckett Simonon Douglas Jodhpur Boots

Beckett Simonon Douglas Tan Jodhpur Boot

* With Exclusive “BU20” Discount Code

Shop Now

Stylish and versatile, the Beckett Simonon Douglas Jodhpur is an original option. What we appreciate about its dressiness is that the ornamention can just be slightly seen under a trouser leg, which results in a streamlined and sleek look.

The Jodhpur boot is spacious but offers just the right level of support. It fits well without being too tight and if you get a half-size above, you’ll easily be able to slip in a few inserts if needed. Furthermore, Beckett Simonon offers foam inserts with all of its orders.

6. Ace Marks Hugo Blucher Boots

Shop Now

Sleek and elegant Italian-made boots, the Hugo pairs nicely with a suit in business professional settings. However, it also looks great with more business casual attire, too.

Thanks to a well-crafted Blake-stitch, the thin profile is both flexible and streamlined. Nevertheless, they’re surprisingly comfortable to wear, especially if you’re on your feet all day!

7. Johnston & Murphy Shearling [Blucher Boot]

Johnston & Murphy Forrester Shearling Boot
Shop Now

With its fleecy genuine shearling lining, these boots are perfect for those colder months and feel like slippers. Furthermore, the storm welt (similar to the Goodyear) offers extra water resistance without sacrificing the ability to replace the soles. You also have a crepe rubber sole for improved traction.

Perfect for those colder months, we’d wear these casually when out and about under the rain. However, they’re also a very tempting option to throw on for your daily commute during winter. In fact, they do actually look rather stylish with business casual or professional attire.

Made from burnished brown Italian calfskin, they’re a significantly cheaper alternative to the Riccardo above. While they won’t be quite as robust or refined, they’re an excellent budget-friendly choice.

8. Johnston & Murphy Copeland Chukka Boots

johnston & murphy forrester chukka boot
Shop Now

From Johnston & Murphy, these Chukkas feature a more artisanal style. With a crepe rubber sole, you can enjoy extra traction and their traditional construction makes them very comfortable even during long periods of time.

These are particularly casual and feel great with jeans and a hoodie during the milder months. However, we’ve been known to sport them with a suit and feel that they’re right at home with more relaxed businesswear styles.

We have a preference for the brown leather as it’s dark enough to be worn across a variety of dress codes. However, we’d also consider them in black should our regular needs be more formal.

9. Taft Branson Boot

Taft Clothing Branson Boot In Honey
Shop Now

Taft is renowned for its rebellious and unorthodox shoe designs. Indeed, it has become a hit among adventurous men who seek to push the boundaries of the businesswear dress code. We love the way the Branson boot marries textile and leather in a unique yet traditional way.

In fact, the quarters are somewhat reminiscent of early 20th century spats, which evokes a somewhat vintage vibe. While perhaps not suitable for more conservative workplaces, it’s a great option if you want to explore a more elaborate wardrobe.

10. Vionic Chase [Orthotic Chukka Boots]

Vionic Chase Tan Chukka Boots
Shop Now

If you’re in dire need of extra comfort, consider these Chukka boots by Vionic. Whilst they’re orthotic shoes, you can barely tell – if at all – that they feature extra comfort for foot disorders. There’s also a podiatrist-designed EVA footbed for extra comfort, which can be removed if you want to replace them.

Although a world apart from the Forrester Chukkas in terms of construction, they’re stylistically very similar. You could happily wear these as casual footwear but even consider pairing them with more formal attire for the office.

Both black or tan options are made from water-resistant suede. We’d opt for the tan as it seems more in line with the formality of both the type of leather and boot design.

Are Dress Boots Always Comfortable?

Allen Edmonds Dalton Wingtip Brogue Boots Paved StreetAlthough dress shoes are renowned for being uncomfortable, dress boots don’t quite have the same reputation. As a type of footwear steeped in rich traditions of work-wear and utilitarian use, they’re often considered to be practical and cosy.

However, that isn’t the case for a lot of boots. In fact, anyone with experience in manual work or the military will likely tell you that boots can be a nightmare.

Nevertheless, they do have some advantages that regular dress shoes don’t. Firstly, the boot shape provides extra ankle support, which takes pressure of your joints when standing or walking.

Furthermore, they tend to be designed with larger and thicker soles, which provides both stability and shock absorption. That said, this is often needed because boots tend to be much heavier than regular shoes.

In this section, we’ll talk about certain characteristics and features that will improve comfort for formal boots.

Ensuring The Right Fit

Allen Edmonds Sullivan Street Winter BootsAs we’ve pointed out in all our comfort-oriented guides, the most important thing to do is make sure that your boots fit! One of the leading causes of foot pain is ill-fitting shoes or boots.

If they’re too large, the feet are loose and will instinctively work to stay in place, which puts strain on them. Meanwhile, boots that are too small will pinch and chafe causing things like bunions.

Allen Edmonds Dalton Wingtip Brogue Boots GrassIf you want to learn more about this, read about how shoes should fit. Although not written specifically for boots, you can apply the same logic. However, you’ll have to keep in mind the quarters too.

Similarly, it’s important to keep your arches in mind. Like foot size, arches vary between people and we all need the right amount of support. Too much support will cause bruised arches whilst too little causes the feet to overpronate and can develop disorders like Plantar Fasciitis.

Overpronation is where your feet roll inwards when you walk. This puts strain on your feet, ankles and hips. When wearing boots, the ankle support means that the feet take the most damage rather than the rest of the body compensating. So remember that arch support is paramount if needed.

Comfortable Dress Boot Features

cordovan boots in shoe boxWhilst quality construction and materials will usually ensure that boots are comfortable, here are a few extra features to look out for:

  • Breathable Materials: Wearing boots can get very hot. Therefore, leather and other natural materials will allow your feet to breathe, which prevents the build up of sweat and blistering.
  • Arch Support: As mentioned above, the right boots for you will just cup your arches enough to ensure they don’t strain themselves when standing or walking.
  • Cushioning: Some boots now feature extra cushion, which contours the feet and provides shock absorption.
  • Stability: Thanks to wider soles and thoughtful construction, good boots will provide stability to prevent an improper stride.
  • Ankle Grip: Shoes will feature collars and notches for this. However, quality boots will carefully brace your ankles to prevent your feet slipping out.

What Next?

Having now read all about the most comfortable dress boots for men, why don’t you consider perusing our related guides?

Shoe Content

Shoe-Homepage Shoe-Style-Guides Shoe-Color-Coordination Shoe-Care-Button Shoe-Reviews