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The Most Expensive Work Boot Brands (And Are They Worth The Money?)

The type of boots that would happily spend all day in the workshop, but wouldn’t look out of place on the shelves of an upscale menswear boutique either.

Words by: Paddy Maddison

Big, burly and built to take a beating, work boots have been keeping blue-collar workers shod for centuries. With thick leather uppers and grippy lugged soles, these rugged stompers are perfectly suited to the rigors of manual labor, but spend a little more on a high-end, luxury pair and they’ll gladly take you places your average steel-toe boot would be hurriedly turned away from.

The most expensive work boots out there might be made from fine materials, have been handcrafted using traditional techniques, have impressive brand heritage, or some combination of all of the above. These are the boots we’re referring to when we talk about ‘luxury work boots’ – the type of boots that would happily spend all day in the workshop, but wouldn’t look out of place on the shelves of an upscale menswear boutique either.

So, how do you spot a pair of expensive work boots, are they worth paying a premium for, and who makes the best ones? Keep reading to learn the answers to all of these questions and more as we delve into the details of one of modern menswear’s must-have pieces of footwear.

What are work boots?

Man wearing daw raw denim jeans and tan leather work boots


‘Work boots’ is an umbrella term that covers lots of different styles, all united by a few key features. A work boot could be a Derby boot, a moc-toe boot, a chukka, or something else entirely, provided it hits some key criteria.

The sole plays a big part in whether a boot is classed as a work boot or not. Generally speaking, work boots will have a thick, durable sole that’s designed for grip either on rough ground or smooth workshop floors. This can mean anything from chunky, lugged commando soles to flat, Christy wedge soles, like those found on Red Wing’s iconic moc-toe boots.

A pair of expensive brown leather work boots for men being polished


Uppers are important, too. Some high-end work boots designed more for aesthetics than functionality might be made from suede, but for the most part, work boots feature thick leather uppers. Leather is the preferred material as it’s more durable and hard-wearing, but some waterproof work boots, such as Timberland’s legendary 6″ boot, use nubuck instead.

Most importantly, work boots have to be sturdy, well-made and built to last. Whether you wear them in the workshop or around the city, they should still be in service years or even decades down the line.

What makes work boots expensive?

4 pairs of high-end men's work boots


This characteristic premium build quality is one of the key factors that makes luxury work boots so expensive. Many brands in this category are either upscale designer labels, heritage workwear brands, or traditional artisanal shoemakers. Manufacturers like these tend to keep production in-house or on local soil, which drives up prices. They also use high-end materials like Italian leathers and expensive sole units, often with Goodyear welting, which inflates costs further still.

A pair of high-end work boots can set the customer back anywhere between £250/$250 and £1,000/$1,200, and while there’s undoubtedly a point of diminishing returns, what you’re paying for is quality, craftsmanship and, in the case of designer labels, clout.

11 luxury work boot brands that are worth every penny

In the market for a pair of high-end work boots but don’t know where to start? Below you’ll find our pick of the most reputable brands making the best premium versions, ranging from upscale Italian designer names to centuries-old American heritage brands. These are the labels to know.

Red Wing

When we picture a work boot, one of Red Wing’s classic 8-inch Moc Toe boots is the first image that comes to mind. These rugged workshop beaters have been in production since the 1950s and have barely changed since. Why? Because how can you improve upon perfection? Functional and stylish in equal measures, these lofty boots are beloved by grizzled mechanics and Williamsburg hipsters alike thanks to their trademark bombproof build and classic looks.

If there’s a better accompaniment to a pair of unwashed raw jeans and heavy flannel shirt we’re yet to find it.


Kleman has a heritage other work boot brands can only dream of. Although a shoemaker and bootmaker by trade, founder René Cléon signed up for the frontlines in World War II. Taken prisoner in 1940 during the Battle of France, Cléon spent five years in captivity in a Stalag in Germany, where he continued to model small leather shoes in his spare time.

At the end of the war in 1945, just weeks following his return home, he formed a team of apprentices and bought his first stitching and assembly machines. Cléon Manufacture was born, specializing in durable, hardwearing footwear for manual workers.

Cléon’s sons, Jacques and Louis-Marie, are now in charge of the company, shortening the name to KLEMAN in 1988 but staying true to the founding principles by keeping all manufacture at its workshop in Anjou, France. You can expect the highest quality materials, unmatched craftsmanship, and a real sense of authenticity from a brand that has bootmaking in its blood.

R.M. Williams

While most American work-boot brands are geared towards life in the workshop, R.M. Williams offers a distinctly Australian twist on the genre. Founded in 1932, the Adelaide-based brand makes hard-wearing riding boots with smooth leather uppers and gusseted ankles.

They’ve been the boots of choice for Australian farmers, ranchers and bushmen for decades, but in recent years, the label has begun increasingly to move into the luxury lifestyle space.

You’ll find beautiful Chelsea boots in premium materials, all handmade in Australia.


Hailing from Portland, Oregon, Danner is another OG American boot brand that really knows its way around the classics, and has created plenty of its own iconic silhouettes too. All of the boots in Danner’s Portland Select collection are heritage styles that are still produced in the brand’s USA factory, just as they have been for almost 100 years.

The range includes styles like the Mountain Light and the Danner Light, which, while definitely more akin to hiking boots in terms of aesthetics, are still firmly within work-boot territory thanks to their sturdy builds and durable, high-quality materials.


Grenson is a historic Northamptonshire shoemaker known for its playful brogues and contemporary twists on classic styles. It also makes some fantastic boots, many of which fall squarely into the work boot category.

Take the Easton for example. It’s an upscale take on a classic moc-toe work boot, rendered in beautiful tumbled leather, with a thick but lightweight commando sole.


Specialising in traditional British country footwear, Tricker’s is another Northamptonshire heritage shoemaker that has been active for almost 200 years. Granted a Royal Warrant in 1989, the brand is well established as one of England’s most respected high-end shoe and boot brands, making everything from loafers to lace-up boots.

The Allan Tramping Boot is a great example of what Tricker’s is capable of when it comes to high-end work boots, boasting a stacked heel, Goodyear welting and Horween Derby leather.


Viberg has been crafting high-quality boots in Canada for almost 100 years. The focus is – and always has been – on producing the absolute finest work boots money can buy. Soles are imported from Italy, cow leather comes from the USA, and water-buffalo hide is brought in from Vietnam to build the brand’s beautiful handmade footwear.

The Service Boot is Viberg’s best-selling and most iconic design. It’s a subtle update on the brand’s original work boot, which was created by founder Edwin Viberg in 1931, featuring a Dainite sole, smooth toe cap and stitchdown construction.

George Cleverley

Founded in 1958, George Cleverley is a relative newcomer to Britain’s traditional shoemaking scene, but the brand still has a well-earned reputation for crafting some of the best footwear in the world.

Cleverley specialises in sleek dress boots that are best paired with tailoring, but there are some more robust styles in the collection too. The Mountain Boot is a prime example, with its Vibram commando sole, thick hiking laces and sturdy build. They’re shearling lined too, making them a great option for trudging through the winter months in style.


Although best known for its shiny puffer jackets, Moncler makes some excellent boots too. The Italian brand’s Vancouver boot borrows its shape from the iconic Timberland 6”, but with lots of luxury details – padded collar, signature tricolor detailing, non-slip lugged rubber sole – that’ll satisfy those looking for a super-premium alternative.

Brunello Cucinelli

If you’re averse to the idea of paying over a grand for a pair of boots then we’d advise you to skip this section. Brunello Cucinelli is not an affordable designer label, but it does make some of the nicest menswear money can buy, from stunning soft tailoring to high-end, handmade footwear.

Styles vary from season to season, but there’s always at least a couple of pairs of rugged-looking work boots in the collection, featuring handmade Italian construction and the absolute finest of materials.


Belstaff was the first brand to use waxed cotton in the production of motorcycle jackets, but there’s more than classic outerwear to this British heritage brand. In case you didn’t already know, Belstaff also makes some seriously badass boots, including styles like the lace-up Alperton and the zip-up Trialmaster motorcycle boot.

One thing they all have in common is that they’re beautifully made, constructed with high-end materials, and built to stand the test of time.