Most Comfortable Dress Boots For Men

Most Comfortable Dress Boots For Men2018-12-03T06:50:46+00:00

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. Blucher Boot: Wolf & Shepherd Breakaway
  2. Blucher Boot: Allen Edmonds Sullivan Street
  3. Wingtip Boot: Ecco Vitrus I
  4. Chukka Boot: Johnston & Murphy Forrester
  5. Blucher Boot: Johnston & Murphy Shearling
  6. Orthotic Chukka Boot: Vionic Chase

See something that you like? Avoid unnecessary scrolling by using the links above to jump ahead.

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

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Quick Buyer’s Guide

Time not on your side? If you use the Quick Buy Guide’s menu below, you can be taken directly to the retailers. Otherwise, just scroll down to learn more about each boot in detail.

Blucher Boot

Wolf & Shepherd Breakaway Boots Feature

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Blucher Boot

Allen Edmonds Sullivan Dress Boot

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Wingtip Boot

ECCO Vitrus I Wingtip Boot

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Chukka Boot

johnston & murphy forrester chukka boot

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Blucher Boot

Johnston & Murphy Forrester Shearling Boot

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Orthotic Chukka Boot

Vionic Chase Tan Chukka Boots

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What Are The Most Comfortable Dress Boots For Men?

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1. Wolf & Shepherd Breakaway [Blucher Boot]

Wolf & Shepherd Breakaway Boots Feature
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Overview

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.

How To Wear

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.

Best Colors

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.

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2. Allen Edmonds Sullivan Street [Blucher Boots]

Allen Edmonds Sullivan Dress Boot
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Overview

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.

How To Wear

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.

Best Colors

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.

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3. Ecco Vitrus I [Wingtip Boot]

ECCO Vitrus I Wingtip Boot
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Overview

With natural calf crust leather from Ecco’s own tanneries, these boots are supple and hug the feet just right. Furthermore, you can benefit from the brand’s own Fluidform technology, which provides extra cushion for all-day comfort.

How To Wear

The unfinished leather is hand buffed and polished, which gives a particularly artisanal appearance to these boots. Therefore, they’re great for more casual wear with jeans and a t-shirt. However, we’ll still consider them for business casual wear too if you throw on a sport jacket and clean dress shirt!

Best Colors

If you want to wear these formally, you could always choose black leather. However, we prefer the natural appearance of the brown and its distressed look.

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4. Johnston & Murphy Forrester [Chukka Boots]

johnston & murphy forrester chukka boot
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Overview

From Johnston & Murphy’s 1850 Collection, these Forrester Chukkas are made to embrace 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.

How To Wear

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.

Best Colors

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.

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5. Johnston & Murphy Shearling [Blucher Boot]

Johnston & Murphy Forrester Shearling Boot
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Overview

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.

How To Wear

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.

Best Colors

We’ve only seen these boots available in burnished brown Italian calsfkin. While this is overall quite stylish, there’s the balmoral cap toe, which offers a touch formality when needed.

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6. Vionic Chase [Orthotic Chukka Boots]

Vionic Chase Tan Chukka Boots
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Overview

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.

How To Wear

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.

Best Colors

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.

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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?

Comfortable Dress Boots Guide
Reviewed by Carlos A., on .
"Unparalleled comfort. Great boots that really help after a long day at work."
Rating: 5.0 ★★★★★

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