Best Boots For Men To Up Your Style Game: The Top 20

Finding the perfect pair of boots for yourself can prove to be quite a challenge. In the quest for the ultimate footwear, there are many things to consider: at Maximonline, style, comfort and practicality are the three factors that top our list. 

With the wide variety of options out there, it’s easy to be overwhelmed by choice. But don’t trip over your laces, we’ve got you covered. Here are our top 20 bootilicious picks: 

1. Clarks Originals Desert Boot

Clarks Desert Boot
Photo from clarksusa.com

Clarks has been the face of the industry for quite some time. Their desert boot was conceptualized around the same time as the invention of the chukka boot. The son of the founder of Clarks saw soldiers wearing the innovative footwear and immediately commissioned boots of a similar design to be made.

This desert boot is truly one of the best boots for men. It is highly versatile and can complement almost any style of clothing. Our recommendations? Try pairing these with denim or even chinos and you’ll immediately up your fashion game.

2. Timberland’s Contrast Collar Boot

Timberland Men's 6 Basic Contrast Collar Boot
Photo from Amazon

Yet another classic brand, Timberland boots can often be seen being worn by celebrities in music videos or out on the streets. Despite its reputation as a “street” brand, Timberland really does produce some of the most durable boots around. 

The Timberland Contrast Collar boot offers a really comfortable fit. The boots are also waterproof so you never have to worry about a rainy day.

Additionally, the classic color also makes it really easy to pull off with a nice pair of denim jeans. Timberlands are one of the best boots for men who like to be hip.

Get Timberland Men’s 6″ Basic Contrast Collar Boot from Amazon.

3. Suede Chelsea Boots by Common Projects

Suede Chelsea Boots
Photo from mrporter.com

The brand Common Projects oozes and epitomizes luxury. Their footwear often makes lists and once again they’ve made this list of the best boots for men. Their Chelsea boots come with the brand’s signature embossed gold serial numbers, and give off a cool yet understated feel. 

Like all Chelsea boots, these boots have elastic sides and a pull tab at the back. The taper of toes is not too drastic either, meaning that you’ll have a comfortable amount of room for your feet. 

4. Grenson Triple Welt Fred Boot

Grenson Triple Welt Fred Boot
Photo from grenson.com

An expert in classics that every man should own, Grenson consistently delivers with its range of boots. The Grenson Triple Welt Fred Boot is no exception.

It has three welts instead of the usual one, making the boot more rugged and watertight.  The shoes are also handmade, ensuring top levels of quality are consistently delivered. 

If your pair suffers some wear and tear, Grenson will refurbish them for you, replacing the worn parts but keeping the parts that have molded to the shape of your foot. Truly a boot that will last a lifetime.

5. Wolverine Original 1000 Mile

WOLVERINE Men's 1000 Mile Fashion Boot
Photo from Amazon

The comic character Wolverine often claims that he’s the best there is at what he does. Well, the brand Wolverine is no different. Their 1000 Mile boots are all handcrafted to ensure quality control. They use premium leather from the Horween leather company and Goodyear welting techniques to allow your boots to be easily re-soled. 

With its classic look and feel, the Wolverine secures a place on our list of best boots for men.

Get WOLVERINE Men’s 1000 Mile Fashion Boot from Amazon. 

6. Dr. Martens 1460 Boot

Dr Martens 1460 boots
Photo from Amazon

We’ve all heard of Dr. Martens. Their iconic boots have found their way into many genres of culture over the years. This particular pair of boots is made from 100% leather. Furthermore, the upper and sole heat-sealed and sewn together for greater adherence and durability in the long run.

Get Dr. Martens – 1460 Original 8-Eye Leather Boots for Men from Amazon. 

7. Mishansha Men’s Winter Boots

Mishansha Mens Winter Ankle Snow Hiking Boots
Photo from Amazon

Boasting a classic design and warm interior, go places with this pair of gorgeous boots. Whether hiking, camping, or even mountaineering, the Mishansha’s solid construction means it is able to withstand even the harshest of weather conditions.

Get Mishansha Mens Winter Ankle Snow Hiking Boots from Amazon. 

8. Ariat Men’s Recon Mid Casual Boot

Ariat Men’s Recon Mid Casual Boot
Photo from Amazon

With a snug and secure fit, it’s easy to fall in love with this pair of high-quality pull-on boots. Its “Golden Grizzly” (tawny brown) shade complements various outfits easily, while a round toe profile makes for extra-comfortable wear, even for prolonged periods of time.

Get Ariat Men’s Recon Mid Casual Boot from Amazon. 

9. The North Face Men’s Chilkat Nylon Boot

The North Face Men's Chilkat Nylon Boot
Photo from Amazon

Keep the cold winter wind out with these fleece-lined boots – Dri-Lex fleece lining effectively blocks out the cold by wrapping your leg in soft warmth. Whether you’re plowing through snow or trekking up a mountain, rubber lugs ensure your safety by increasing the amount of traction produced. A trustworthy companion for any occasion.

Get The North Face Men’s Chilkat Nylon Boot from Amazon. 

10. CLARKS Men’s Tilden Zip Ii Waterproof Boot Ankle

CLARKS Men's Tilden Zip Ii Waterproof Boot Ankle
Photo from Amazon

With a full-grain leather build and comfortable features such as a durable outsole, these leather boots are big on both aesthetics and functionality. As a result of its waterproof ability, you’ll never have to worry about wet, soggy boots again.

Get CLARKS Men’s Tilden Zip Ii Waterproof Boot Ankle from Amazon. 

11. Bruno Marc Men’s Suede Leather Chukka Ankle Boots

Bruno Marc Men's Suede Leather Chukka Ankle Boots
Photo from Amazon

Upgrade your wardrobe instantly by opting for these Bruno Marc ankle boots: with elastic side panels for ease of wear, a cushioned footbed for additional comfort, and a wide variety of colors to select from, you definitely can’t go wrong with these.

Get Bruno Marc Men’s Suede Leather Chukka Ankle Boots from Amazon. 

12. DC Men’s Woodland

DC Men's Woodland
Photo from Amazon

Lightweight and comfortable, these 100% leather-and-textile boots are guaranteed to keep your feet warm, even in the middle of winter. While perfect for nearly any activity, these leather boots function especially well as casual/skating shoes, and (like its name implies) excel when it comes to hikes.

Get DC Men’s Woodland from Amazon. 

13. Calvin Klein Men’s Alixander Chelsea Boot

Calvin Klein Men's Alixander Chelsea Boot
Photo from Amazon

A sophisticated choice, don Calvin Klein’s Alixander Chelsea boots to instantly become the star of the show. Sleek and minimalistic design aside, one of its biggest pros lies in its construction: double-stretch gore ensures great stretchability, breathability, and longevity of these beauties in the long run.

Get Calvin Klein Men’s Alixander Chelsea Boot from Amazon. 

14. J’aime Aldo Men’s 76631 Leather Lined Ankle High Square Toe Chelsea Dress Boots

J'aime Aldo Men's 76631 Leather Lined Ankle High Square Toe Chelsea Dress Boots
Photo from Amazon

These square-toed Chelsea boots go well with virtually any outfit, and are perfect for everyday wear. Featuring a rubber sole and a 1″ block heel, take every step forward with confidence.

Get J’aime Aldo Men’s 76631 Leather Lined Ankle High Square Toe Chelsea Dress Boots from Amazon. 

15. Jazame Men’s McVey Distressed Moto Riding Ankle Bootie Chelsea Dress Boots

Jazame Men's McVey Distressed Moto Riding Ankle Bootie Chelsea Dress Boots
Photo from Amazon

Classic rules and this pair of boots is proof of just that: with a buckle design and modern distressed upper, the Jazame Men’s McVey will see you from the workplace to the party after. Rock on.

Get Jazame Men’s McVey Distressed Moto Riding Ankle Bootie Chelsea Dress Boots from Amazon. 

16. Rockport Men’s Rugged Bucks Waterproof Boot

Rockport Men's Rugged Bucks Waterproof Boot
Photo from Amazon

Hydro-Shield waterproofing construction guarantees warm and dry feet all day, errday. This one’s a rugged, mid-cut boot with padded collar. It utilizes a comfort system that is designed specifically to provide lightweight shock absorption.

Get Rockport Men’s Rugged Bucks Waterproof Boot from Amazon. 

17. R RUNFUN Men’s camo Waterproof Lightweight Hunting Boots

R RUNFUN Men's camo Waterproof Lightweight Hunting Boots
Photo from Amazon

Lightweight and breathable, creep up on your next kill with these hunting boots. An anti-slip sole and insulated 400G 3M Thinsulate effectively prevent falls and supports your every move, so you can shoot/gun down your prey in next to no time.

Get R RUNFUN Men’s camo Waterproof Lightweight Hunting Boots from Amazon. 

18. FitFlop Men’s Boot, Zackery Desert

FitFlop Men's Boot, Zackery Desert
Photo from Amazon

Made from 100% suede, this boot features a slip-resistant rubber outsole and has been certified with the American Podiatric Medical Association (APMA) Seal of Acceptance for promoting good foot health. To add on to that, it comes with vulcanized-effect midsoles and a seamless built-in arch contour!

Get FitFlop Men’s Boot, Zackery Desert from Amazon.

19. Caterpillar Men’s Threshold Waterproof Steel Toe Industrial Boot

Caterpillar Men's Threshold Waterproof Steel Toe Industrial Boot
Photo from Amazon

Featuring a breathable leather upper, waterproof membrane and steel toe, this is about as durable a boot as you can get. Contrary to its rather “industrial” look, this pair of boots performs excellently in everyday situations too.

Get Caterpillar Men’s Threshold Waterproof Steel Toe Industrial Boot from Amazon.

20. Merrell Men’s Moab 2 Vent Mid Hiking Boot

Merrell Men's Moab 2 Vent Mid Hiking Boot
Photo from Amazon

Pack up and lace up a pair of these for your next hiking trip: highly breathable and durable, the Moab 2 makes a trustworthy companion for any outdoor excursion. While it comes with a ton of cool features, you’ll have to wear it for yourself to believe it.

Get Merrell Men’s Moab 2 Vent Mid Hiking Boot from Amazon.


Whether for work, casual wear or both, you’re bound to find your ideal pair of boots from this list. Make a fashion statement and stand out from the crowd today!

Alternatively, if boots are not quite your thing, check out these awesome walking shoes for men. 

Mr Maxim
Mr Maxim is your go-to guy for all things men's lifestyle. If you need help getting your mojo together, Mr Maxim has all the tips you need to survive as a modern man in the 21st century.

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