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The 10 Best Boots For The Modern Man: Awesome 2024 Line Up

Boots are a man’s best option footwear. They are robust, masculine, for the most part durable and surprisingly varied in options. While shoes range so widely that we could write an entire book just on the variants that exist, boots have enough options and choices for every occasion without the overwhelming number of options standard shoes have.

best boots for men

The good thing about a quality pair of boots is that firstly, they last long, nearly a lifetime if the quality is high enough. As well as their durability, a good pair of boots, like some leather wingtips can be easily transitioned from casual to smart. Boots are awesome in rain or shine, and even more useful in the winter snow. Below are ten shoes of five types to add to your footwear arsenal.

​Here is a video on how to buy the perfect boots:

Before we get into the top 20 best boots for men, it’s best to address why you need a pair of boots. The modern man needs a pair of boots for two reasons.

    • The first reason is that your footwear is the basis of your entire movement. A comfortable pair of boots or shoes will make the difference between enjoying the average 3,000 steps you take a day and slowly walking yourself into injury and pain. Taking time to choose the right footwear is an investment in your financial and general future.
    • The second reason you should care about what you put on your feet is that women will judge you by it. Women often claim they judge a man by what he chooses to walk in. Looking good from head to the toe is a reason in itself to choose a good pair of boots.​

Check out this video:

The Best Boots for the Modern Man

The Chelsea Boot

With fashion being as cyclical as it is, the 1960's were always going to come back into fashion. The 60's were a time for bright garish colors, interesting foppish hair, and adventurous fashion.

It is in this time that the Chelsea boot found its feet. But the 60's classic actually dates back to the Victorian era where it was designed and invented by J. Sparkes-Hall, who was boot-maker to Queen Victoria herself.

This English classic has once again returned to the world of fashion and is seen on the feet of everyone from Taylor Swift to soccer dads at the park. These are the best two Chelsea boots on the market, one is high-street and the other more high-fashion.

High End- O’Keeffe: Bristol Distressed Suede Chelsea Boots ($550)

               Bristol Distressed Suede Chelsea Boots

These Italian made shoes are perfect to pair with slim jeans and a classic oxford shirt, and with a price tag like that you’d expect to get some long wear out of them, and with Goodyear welted soles you can be rest-assured they will last.

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High street: Dr Martens Original Chelsea Boots ($220)

Dr Martens Original Chelsea Boots

Dr. Martens are synonymous with high street quality, and these 100% leather pair of Chelsea Boots for under $250 is a steal. The rubber heels and Goodyear welted soles means that $220 will last you years.

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The Chukka Boot

The Chukka boot is certainly the boot of the last few years, being adored by the likes of Zac Efron and David Beckham.

While the Chukka filling the shelves of high street brands and on the feet of every fashion conscious male who has ever seen a Topman, the boot found its humble beginnings on the feet of British WWII soldiers in the Western Desert Campaign in Libya and Egypt.

This is why some Chukka boots are sometimes called desert boots. The simple structure and design of these boots lends them to casual wear more than formal attire, most commonly being paired with jeans and a t-shirt.

High End: Tod’s Suede Chukka Boots ($595)

             Tod’s Suede Chukka Boots

Like most of footwear fashion at the moment, these boots are suede. But it’s the quality of the suede and of the Tod’s which make it the best Chukka out there. As with any quality shoe, it was made in Italy, this combined with the rugged brick red of the boot certainly encourages its expensive purchase.

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High street: Hawking McGill Leather Desert Boot ($69)

Hawking McGill Leather Desert Boots

At just over a tenth of the price of the high-end Tod’s, these leather Chukkas from Hawkings McGill are a great option if you are strapped for cash but still want to keep up with the modern style. For $69 the quality is surprisingly good, with a durable rubber heel and well-crafted leather. It is a bargain

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The Work Boot

The manly man’s boot. The boot for the ages. The boot of the gruff and old and the young hipster alike.

While work boots may transition from a bit of gardening to going to your local bar quite well, they are most certainly not for every occasion. However, they are a great choice for those of you who want a comfortable, extremely durable and fashionable enough boots.

The good thing about getting a pair of work boots is that the longer you have them (and they will last for long) the more fashionable they get. A pair of brand new, mega shiny and altogether pristine pair of work boots are less fashionable than those which have been used for a while.

It’s the authenticity of the real-life style which gives them their fashion credentials.

High End: Balenciaga-Lug-Sole Leather Lace-Up Boots ($1,185)

                 Balenciaga-Lug-Sole Leather Lace-Up Boots

While these are inevitably the best quality, best looking and most likely best work boots you can buy, you must be able to live with spending more on these boots than your rent. If you can live with that, then these exceptionally designed work boots will be a great addition to your winter garb.

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High Street: Red Wing Rubber Sole Leather Boots ($260)

 Red Wing Rubber Sole Leather Boots

While not cheap, this American classic is perfect for both work and play. The more stylish version of the work boot gives you the option to get hands dirty and go to a party. The rubber soles are designed to be durable and give you as much comfort as possible while the triple stitched leather ensures a long life for the boots.

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The Biker Boot

This boot was eponymously made famous by bikers and taken into the fashion world more recently.

The rougher and more bad-ass style lends itself to non-formal wear, but can surprisingly be paired with a smart trouser (if the boot is right). Biker boots work best with some well-worn boot cut jeans and matching biker jacket.

High End: Belstaff- Trialmaster Leather Boots ($725)

          Belstaff Trialmaster Leather Boots

These really are the crème de la crème of biker boots; comfort, style, heritage, quality. If you are capable of forking out the $725, do it it’s worth it.

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Highstreet: Topman-Black Suede Buckle Boots ($150)

           Topman black suede boots

Although Topman have decided to name them Buckle Boots, they are in fact Biker boots. With a Cuban heel and pointed toe, the high street variation to the biker boot is both on trend and affordable. If you’re not sure about investing in an expensive pair, try these out and see if you like them.

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Brogue Boots

The brogue, which has its origins in Ireland, has more recently been found brandished on the toes of large leather boots.

The classic design looks good in both high fashion and high street. However, the quality is certainly different. While the tan leather brogue boot is the most common, the number of variants and more creative designs mean you can get some real gems.

High End: Grenson- Fred-Grained Leather Brogue Boots($465)

Grenson Fred Grained Leather Brogue Boots

A wonderfully designed boot from Grenson, perfect for summer and winter. The detail of the brogue design combined with the thick rubber heel means that you will be comfy and stylish for years to come.

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High Street: ASOS Brogue Boot in Burgundy Leather ($111)

                       ASOS Brogue Boot in Burgundy Leather

Why choose a tan or black pair of boots when you can have the lovely hue of a burgundy pair. This bargain from ASOS is a great choice for just mucking around in. The quality may not be the same as the Grenson’s but for the price, the design is pretty amazing.

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There you have it, 10 boots to try. Whether you go high-end or high-street just grab a pair. A pair of boots is simply a must-have for the modern man. Bonus: if you’re shorter, they add 2 inches to your height.

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Written by Terrence Kennedy

Terrence Kennedy is the man’s man on a journey to self-discovery. A traveler, extreme sports aficionado, an observant wanderer, a DIY-Know-How, an ultimate outsider and a documentarist of culture, sex, dating, relationship, fashion, style and gentleman's etiquette. He has learned a lot through his escapades, and is happy to pass that knowledge on to you.