Whatever dress code you have in mind, you may be looking for the most stylish boots possible. Although style is subject and fashion tends to be fleeting, there’s a variety of different designs that you could choose.

Between our reviews and our own tests, we’ve assembled the Most Stylish Men’s Boots that you can also buy online:

  1. Blucher Boot: Johnston & Murphy Bryson
  2. Blucher Boot: Wolverine 1000-Mile Original
  3. Chelsea Boot: CARLOS by Carlos Santana 1947
  4. Wingtip Boot: Allen Edmonds Dalton
  5. Chukka Boot: Johnston & Murphy Forrester
  6. Chukka Boot: CARLOS by Carlos Santana Corazón
  7. Wingtip Chukka Boot: Wolverine Harwell
  8. Work Boot: Danner Bull Run Christy

If something has caught your eye, you can use the above links to jump ahead. We’ll also briefly cover the different types of boot style and how their styles are timeless rather than simply fashionable.

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Quick Buyer’s Guide

Don’t want to spend time reading up on each boot? Use the Quick Buy Guide to pick a style and be taken directly to the retailer. Otherwise, you can scroll down to learn each boot’s details.

Blucher Boot

Johnston & Murphy Bryson Cap Toe Boot

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Blucher Boot

Wolverine Original 1000 Mile Cordovan Boot

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Chelsea Boot

CARLOS by Carlos Santana 1947 Chelsea Boot

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Wingtip Boot

Allen Edmonds Dalton Wingtip Boots

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Chukka Boot

johnston & murphy forrester chukka boot

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Chukka Boot

CARLOS by Carlos Santana Corazon Chukka Boot

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Wingtip Chukka

Wolverine Harwell Wingtip Chukka

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Work Boot

Danner Bull Run Christy Winter Boot

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What Are The Most Stylish Men’s Boots?

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1. Johnston & Murphy Bryson [Blucher Boot]

Johnston & Murphy Bryson Cap Toe Boot
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Overview

An iconic blucher-styled boot, the Bryson’s come from Johnston & Murphy’s 1850 Collection, which celebrates artisanal craftsmanship. Made from premium calfskin, these Italian hand-crafted boots are remarkably supple thanks to the dip-dye and washing process.

How To Wear

Thanks to a pebbled effect, they’re quite casual but this is reined in with the cap toe. This allows them to be worn across a spectrum of dress codes from simply casual all the way to the lower end of business professional. However, they look their best as business casual boots with a pair of dark jeans and a sport jacket.

Best Colors

The brown is beautifully burnished and makes for a stunning boot that’s very versatile. However, the black is quite good and actually quite casual too given it’s matte and almost grey-coloured finish.

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2. Wolverine 1000 Mile Boot [Blucher Boots]

Wolverine Original 1000 Mile Cordovan Boot
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Overview

An American icon that dates back to the early 1910s, the original 1000-Mile boots were workwear. However, their quality and design is absolutely timeless and has gone on to be emblematic of true Americana style. From Horween Leather Company materials to a Goodyear welt, it’s a boot that will last forever.

How To Wear

Casually or formally, these are boots are so woven into America’s cultural fabric that they’re almost external to dress codes. Whilst you won’t be seeing us sporting them with black tie, they’re great with either a classic business professional suit or vintage denim and a checked shirt.

Best Colors

We particularly love the Cordovan colour, which is very versatile and will fit most occasions. However, there’s also rust tan or brown that works well too. Otherwise, the black option can be worn more formally.

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3. CARLOS by Carlos Santana 1947 [Chelsea Boot]

CARLOS by Carlos Santana 1947 Chelsea Boot
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Overview

For something completely different, check out these beautifully ornate Chelsea boots by Carlos Santana. The streamlined wingtip and brogue details are mouthwatering and the quality speaks for itself with a Goodyear welt construction and European Box Calf full grain leather upper.

How To Wear

These multi-faceted boots are ideal for a number of dress codes. Whether a suit or slim-fitting jeans, they’re stylish and will add a touch of flair to whatever formality you require.

Best Colors

Depending on your tastes and needs, you can choose between either black or tan full-grain leather. If you want something that’s flashy and more versatile in the casual range, then opt for the tan, which is currently only available on Zappos for the same price but sold out on the brand’s official site. Alternatively, the black is great for more formal occasions.

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4. Allen Edmonds Dalton Wingtip [Brogue Boots]

Allen Edmonds Dalton Wingtip Boots
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Overview

Allen Edmonds is a heritage brand that prides itself in quality and durability. Their classic wingtip boots are a testament to their craftsmanship and feature beautiful brogue ornamentation. The boots are made with smooth calfskin and Dainite soles, which are then constructed using a 360° Goodyear welt.

How To Wear

Again, these are very versatile and probably more so than the other boots featured above. They’re great in business professional attire but can also be comfortably worn casually with jeans.

Best Colors

Without the Dainite soles, there’s a whole spectrum of colours available including various burgundies and tan. However, the Dainite soles are one of the best perks of these boots! In this case, you’ll be able to choose between either black or brown. We prefer the black but both have their advantages.

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5. Johnston & Murphy Forrester [Chukka Boots]

johnston & murphy forrester chukka boot
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Overview

Another addition from Johnston & Murphy’s 1850 Collection, these classic chukkas exude the artisanal style that the series embodies. With a crepe rubber sole, they’re real chukkas but also look and feel fantastic.

How To Wear

Although leaning more towards the casual end of the spectrum, it’s not impossible to wear these with a suit. However, we find that they look their best either casually or with a slight business flair.

Best Colors

The formal black feels a bit out of place given the boot style. Instead, we’d opt for the brown, which is much more appropriate and versatile to wear with a variety of styles.

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6. CARLOS by Carlos Santana Corazón [Chukka Boot]

CARLOS by Carlos Santana Corazon Chukka Boot
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Overview

Another stylish boot from Carlos Santana, these elegant brogues are a completely different take on the style from the Forresters above. The smooth leather has a delicate cut to it and the shoe is constructed using Blake stitching.

How To Wear

More elegant than the Forrester, the Corazón is also more formal thanks to its refined and delicate structure. Nevertheless, it’s still a boot that can be worn as casually as you’d like. However, you can also wear it more formally with a business suit with much more ease.

Best Colors

What’s great is that these are available in both suede of full-grain calfskin leather in both black or brown. We prefer the black calfskin as it has a more dignified look but they’re all excellent and give you a wide choice.

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7. Wolverine Harwell [Chukka Boot]

Wolverine Harwell Wingtip Chukka
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Overview

Another chukka you say? Yes but Wolverine’s approach to the classic style is just as unique as the former two. Part of the brand’s 1000-Mile Collection, these also feature a Goodyear welt. You have extra eyelets compared to conventional brogues and a refined brogue wingtip ornamentation.

How To Wear

Great as either a business casual or casual choice, these could even be worn professionally with the right colour leather. They’ll look great in either jeans or ironed chinos and are versatile for a number of different wardrobe styles.

Best Colors

There’s a choice of either black or brown full-grain leather, which are overall quit casual. As the black chukkas feature some brown accents in the midsole, they’re not as formal as fully-black footwear.

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8. Danner Bull Run Christy [Work Boots]

Danner Bull Run Christy Winter Boot
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Overview

We were at first reluctant to feature work boots in this list but we were so impressed by Danner’s American-made F2892-11 approved soft toe creations. Whilst they’re very dapper for contractors, they’re also very stylish for even casual wear.

How To Wear

These are distinctively casual boots that look their best when paired with jeans and a rustic Americana-style shirt. However, we’d also dare to wear them with some more rugged business casual styles too.

Best Colors

Thanks to their high-quality oiled leather, you can treat to leather to develop the style that you’d prefer. You can leave them to age naturally for a distressed vintage look or polish them up for a nice buff.

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What Factors Contribute To Boot Style?

Allen Edmonds Dalton Wingtip Brogue Boots Formal LouvreCertainly, style is very much a subjective concept with many different schools of thought. However, whatever style you may prefer, you’ll know that it’s something that goes far deeper than fashion.

As we quipped in the introduction, fashion fades whilst style is eternal. But beyond quoting Yves Saint Laurent, it’s important to recognise the distinction between the two.

By suggesting that boots are fashionable implies that their aesthetic is rooted in a period of time and its popularity is largely dependant on popular trends. However, if you are to refer to them as stylish, it suggests that they overcome the transcend the temporal limitations of fashion.

Therefore, style is something that acts as something of a constant and may play a significant role in influencing fashion instead. As such, we put a lot of emphasis on style of fashion as it carries more substance and will provide better long-term guidance.

However, what factors render a boot stylish and how do they overcome the limitations of fashion?

Boot Quality

Allen Edmonds Dalton Wingtip Brogue Boot Dianite SoleWe believe that one of the most fundamental contributions to style is deeply rooted in the garment’s quality. When talking about boots, we refer to its construction and materials.

Brands such as Wolverine, Allen Edmonds, Danner and Red Wing don’t simply make a name for themselves spontaneously. This often stems from generations of hard work, attention to detail and dedication all fuelled by passion for their craft.

Of course, these brands have all become fashionable at least once since their humble beginnings. However, they’ve been immortalised thanks to their wealth of clients who have depended on their boots for decades.

The above brands take great pride in where their materials are sourced. For instance, Wolverine will often publicise that their leathers come from the Horween Leather Company. Furthermore, they continue to use high-quality and traditional methods for constructing their boots such as the Goodyear welt.

Finally, they each have their own stories and histories, which are what have rendered them unique. These brands continue to respect this heritage with choices such as continuing to craft their wares in the USA.

This quality is reflected in the designs of their boots, which exudes both passion and style.

Boot Versatility

wolverine 1000 mile boots with odd jacketYou may also have noticed that we’ve indicated that many of the above boots are extremely versatile and can be worn across a broad spectrum of dress codes. This is a hallmark of particularly stylish boots that use understated elegance rather than brash fashion to influence their designs.

As the boots aren’t strictly utilitarian or single use, they gain a multi-faceted character, which allows them to be worn across a multitude of occasions. Their innate quality plays an important role in this and the Danner work boots are an excellent example.

For instance, their Christy Bull Run boots were designed primarily for heavy-duty labour. However, because of the dedication and resources invested into these shoes, they are of excellent quality. Consequently, they’re very attractive and stylish boots, which means they overcome their original purpose.

Final Thoughts

In the end, style is a very subjective matter and remarkably complex to explain. There are many contributing factors to a boot’s style but we have used the above principles in order to find the most exquisite specimens of men’s footwear.

The boots above are more than just boots but represent decades of multi-generational craftsmanship. As such, they represent American and Continental style at their finest.

What Next?

Having now explored the most stylish boots for men, consider checking out some of our related shoe and boot guides:

Most Stylish Boots Guide
Reviewed by Alfred R., on .
"Really cool boots. Love these fantastic boots. Not just stylish but great quality too!!"
Rating: 5.0 ★★★★★

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