Whatever dress code you have in mind, and whether you believe in “boot season” or not, you may be looking for the most stylish men’s boots possible. Although style is subjective and fashion tends to be fleeting, there’s a variety of different boot 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. Chelsea Boots: Amberjack The Chelsea
  2. Chukka Boots: Beckett Simonon Lopez
  3. Cap Toe Boots: Johnston & Murphy Bryson
  4. Dress Boot: Wolverine 1000-Mile Original
  5. Chelsea Boot: CARLOS by Carlos Santana Mantra
  6. Wingtip Boot: Allen Edmonds Dalton
  7. Leather Chukka Boots: Johnston & Murphy Forrester
  8. Desert Boots: Clarks Original
  9. Wingtip Chukka Boot: Wolverine Harwell
  10. Work Boot: Thorogood 6″ Moc Toe

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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What Are The Most Stylish Men’s Boot Brands?

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1. Amberjack [Chelsea Boots]

Amberjack Stylish Chelsea Boots In Smooth Leather
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Since the brand’s inception, Amberjack shoes were designed with both style and comfort in mind. Given the brand’s success, it’s clear that they’re doing something right.

The Original, a blucher style, was the brand’s first offering. Most recently, a wide array of Chelsea boots have been introduced.

Crafted with heat-activated arch support and dual-density, high-performance outsoles, these Chelseas are anything but lacking in the comfort department. Coupled with fine Italian suede or A-grade leather uppers, the quality element is likewise present.

How To Wear

As mentioned, Amberjack offers its Chelsea boots in a number of different colors and textures. The suede options offer a more contemporary, night-out-on-the-town style, while the full-grain leather uppers allow you to bring these into business casual workspaces.

Best Colors

Broadly speaking, it’s difficult to settle on just one pair of Amberjack Chelsea boots.

For instance, the Chestnut is likely the most versatile color. However, the Dune suede boots offer the light-colored Chelsea style that’s become increasingly popular in recent years. Furthermore, if you enjoy darker ensembles, the Midnights are a must-have. Keep in mind that suede will repel water which makes it ideal for wet weather.

Ultimately, the hardest choice is not going to be whether to get them or not, but rather which pair to purchase next.

2. Beckett Simonon Lopez [Chukka Boots]

Lopez Black Service Boot On Feet

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Inspired by the classic World War II service boot design, Beckett Simonon has reinvigorated it with a fresh new take.

Robust yet elegant thanks to the Italian calfskin and rounded toe, it’s hard to believe that you can pick up these combat boots for less than $200!

How To Wear

If you go for a dark color, you could potentially wear the Lopez with a suit. However, if you’re more partial to lighter leather uppers, you can easily wear these combat boots with chinos or jeans. Regardless of color choice, the rubber soles will ensure safe, all-weather wear.

Best Colors

As mentioned above, darker colors such as black or brown can make these combat boots come off as quite formal. If you’re looking to produce a more casual effect, opt instead for the Bordeaux or tan leather.

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3. Johnston & Murphy Bryson [Cap Toe Boot]

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

How To Wear

The pebbled effect of the leather makes these quite casual, yet this aspect 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 dress 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 its matte and almost grey-colored finish.

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4. Wolverine 1000 Mile Boot [Dress Boots]

Wolverine Original 1000 Mile Cordovan Boot
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An American icon that dates back to the early 1910s, the original 1000-Mile service 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 and leather sole, it’s a boot that will last forever. There’s a reason why so many deem a pair of these as the best boots for men, period.

How To Wear

Casually or formally, these combat 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 color, 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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5. CARLOS by Carlos Santana Mantra [Chelsea Boot]

Carlos by Carlos Santana Mantra Chelsea Boot
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For something completely different, check out the beautifully ornate Mantra Chelsea boot by Carlos Santana. The streamlined upper with broguing and contrast pull-tabs are mouthwatering and the quality speaks for itself with the padded footbed and full-grain leather upper.

How To Wear

These multi-faceted Chelsea 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 suede or tan full-grain leather. If you want something that’s flashy and more versatile in the casual range, then opt for the tan. Alternatively, black suede or calfskin are great for more formal occasions.

6. Allen Edmonds Dalton Wingtip [Brogue Boots]

Allen Edmonds Dalton Wingtip Boots
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Allen Edmonds is a heritage brand that prides itself on quality and durability. Their classic wingtip boots are a testament to their craftsmanship and feature beautiful brogue ornamentation.

These dress boots are made with smooth calfskin and Dainite soles, which are then constructed using a 360° Goodyear welt that renders them a completely waterproof boot.

How To Wear

Again, these are very versatile and perhaps even more so than the other boots featured above. They’re great in business professional attire but can also be comfortably integrated into casual wear, such as with jeans.

Best Colors

Without the Dainite soles, there’s a whole spectrum of colors 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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7. Johnston & Murphy Forrester [Leather Chukka Boots]

johnston & murphy forrester chukka boot
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Another addition from Johnston & Murphy’s 1850 Collection, these classic ankle boots 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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8. Clarks Originals [Desert Boot]

Clarks Tan Desert Boots
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Clarks is the original purveyor of the desert boot. Indeed, any pair of desert boots you’ve ever seen before is a spawn of Clarks’ original style introduced in 1950.

If these seem oddly similar to the above Johnston & Murphy Chukka ankle boots, that’s because desert boots are technically Chukkas, except they’re called Desert boots when they boast a suede upper and a crepe sole.

How To Wear

Any style of desert boot is going to be rather casual; as the name implies, these were intended to be worn in the desert.

That being said, the desert boot has become so popular that it’s managed to escape the casual realm. They’re regularly worn with jeans, chinos, and other casual trousers as part of dress casual ensembles.

For more details on seasonality and properly pairing your favorite style of Desert boot, visit our standalone guide here.

Best Colors

The most traditional Desert boot color is the style featured above with a sand-toned suede upper.

Nonetheless, Clarks also offers the Beeswax option which is made with vegan leather uppers. Darker tones are likely to be more versatile but it goes without saying that if you’re going for your first pair of Desert boots, the sand suede upper is probably the best choice.

9. Wolverine Harwell [Chukka Boot]

Wolverine Harwell Wingtip Chukka
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Another chukka you say? Yes, but Wolverine’s approach to the classic Chukka boots 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 dress boot choice, these could even be worn professionally with the right color 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 itself is quite 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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10. Thorogood 6″ Moc Toe Boots [Work Boots]

Thorogood 6in Moc Toe Boots Stylish Option
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We were at first reluctant to include work boots such as these Thorogood moc-toe boots in this list but we were quite impressed by these Made-in-USA soft toe creations. Whilst they’re very dapper for contractors, they’re also very stylish for casual outfits.

How To Wear

As a moc-toe boot with chunky rubber soles, these are a distinctively casual work boot style that looks 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

Tobacco is often the most popular choice when it comes to the Thorogood Moc-Toe Work Boot. However, the Dirty Brown Crazyhorse variety is quite handsome and arguably more stylish than the former leather option.

If you’ve never owned a pair of these, perhaps you’d rather stick with the traditional Tobacco. Otherwise, the Brown Crazyhorse provides the classic style with an updated look.

What To Consider When Shopping For Stylish Men’s Boots?

Allen Edmonds Dalton Wingtip Brogue Boots Formal Louvre

Certainly, 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 recognize 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 dependent on popular trends. However, if you are to refer to them as stylish, it suggests that they’ve succeeded in transcending 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 Sole

We believe that one of the most fundamental contributions to style is deeply rooted in a garment’s quality. When talking about boots, we refer to their construction and materials.

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

Of course, these brands have all become fashionable at least once since their humble beginnings. However, they’ve been immortalized after having their boots worn by devoted clients for decades.

The above boot brands take great pride in where their materials are sourced. For instance, Wolverine will often publicize that their leathers come from the famed Horween Leather Company; if you’re unfamiliar with Horween, they’re known as purveyors of very high-quality leather. Indeed, such premium materials can elevate even a work boot out of the casual footwear realm.

Furthermore, these boot manufacturers continue to use high-quality and traditional methods for constructing their boots, such as the Goodyear welt, into the modern-day.

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 whenever possible.

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

Boot Versatility

wolverine 1000 mile boots with odd jacket

You may also have noticed that we’ve indicated that many of the above boots are extremely adaptable 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 Thorogood work boots highlighted above are an excellent example.

For instance, their Moc Toe boots were designed primarily for heavy-duty labor. However, because of the dedication and resources invested into these shoes, they are of excellent quality. Consequently, they’re a very stylish and versatile boot and as such, they’ve managed to 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 men’s boots.

The boots above are more than just boots but represent decades of multi-generational craftsmanship. As such, they represent American and Continental styles 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:

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