10 Most Expensive Work Boots You Can Buy

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Work boots come in many styles of construction that work differently depending on the industry they’re designed for. These include steel-toe, composite-toe, electrical hazard, insulated, and oil-resistant boots, plus different combinations of each.

The price of these boots varies depending on the quality of the construction, the brand, and the materials used.

We compiled a list of the 10 most expensive work boots to show that fashion and functionality aren’t always opposites. They can be best friends in fashion.

10. Rick Owens Beatle Bozo Tractor Boot

Price: $1,350
Color: Black
Brand: Rick Owens
Rick Owens Beatle Bozo Tractor Boot
photo source: Vrsnl

The Rick Owens Beatle Bozo Tractor Boot is a work boot made in Italy. Its construction includes elastic side panels, leather lining, a synthetic outsole, and a round-toe shape.

These boots were made in Italy, so you’ll have to import them from the manufacturer or try to hunt down your size on the aftermarket.

These black mid-calf work boots retail for around $1,350.

Did you know?

Rick Owens is a luxury fashion line started in 1994 on Hollywood Boulevard to make elite movie star couture in the form of Owens’ radical designs. Richard Saturnino Owens got his start at the Otis College of Art and Design, moving on to making draperies and avant-garde fashion statements with what he calls “deconstructed garments.”

These boots are among the more straightforward fashion creations that bear his name.


9. Brushed Calfskin Ankle Boots with Extra-light Sole

Price: $1,380.36
Color: Black
Brand: Dolce & Gabbana
Brushed Calfskin Ankle Boots with Extra-light Sole
photo source: Dolce Gabbana

The shoes listed as Brushed Calfskin Ankle Boots with Extra-light Sole were made by the luxury fashion house, Dolce & Gabbana. They balance a contemporary and urban fashion style in these Bernini ankle boots. The material is brushed luxury calfskin, which has its signature soft shininess.

The insoles, however, are made from leather with inserts made from quilted satin. The serrated sole is extra-light. These Italian boots are listed for sale on D&G’s eCommerce platform for $1,380.36.

Did you know?

The Italian town Legnano served as the site of Dolce & Gabbana’s founding when Domenico Dolce and Stefano Gabbana got together in 1985 to revolutionize fashion. Their first designs were for swimsuits and underwear. They’ve also won awards for perfume.


8. The Chelsea Boot

Price: $1,450
Color: Green and black
Brand: Bottega Veneta
The Chelsea Boot
photo source: Bottega Veneta

The Chelsea Boot costs the same no matter its color. Bottega Veneta sells them in green, black, taupe, and more for $1,450. The boots are mid-calf in length, made from vegetable-tanned calfskin with rubberized trim at the sole and welt.

The sides of the boots are elasticized gusset to contrast with the buffed calfskin, including the pull-loop. The outsoles are made from treaded rubber to enhance their grip, giving them the functionality of work boots despite their luxury appearance.

Did you know?

The fashion brand Bottega Veneta was founded in 1966 in Milan, Italy. They specialize in fashionable handbags, ready-to-wear clothes, accessories, and of course, shoes. They have 268 stores and a revenue of about 1.17 billion euros every year.


7. Beige & Orange The North Face Edition Ankle Boots

Price: $1,490
Color: Orange and brown
Brand: Gucci
Beige & Orange The North Face Edition Ankle Boots
photo source: SSense

The Beige & Orange The North Face Edition Ankle Boots by the luxury fashion designer, Gucci, are definitely not your average work boots. They’re ankle-high boots made from paneled grained leather and canvas, blocked in beige, brown, and orange sections.

The logo is embroidered on the outside of the boot.

The midsole is made from stacked leather while the outside is treated rubber. The lining is buffed leather. The lace closure is bright red and white, and the hardware is gunmetal grey.

These work boots are part of a fashion collaboration between the Gucci and The North Face brands, made in Italy, and sold for $1,490.

Did you know?

The outdoor recreational clothing brand, The North Face, was started in 1968 to give climbers expertly crafted outdoor clothing, including footwear. Combined with Gucci, their workman-focused designs were twisted into these stylish peachy creations.


6. Tom Ford Leather Patch Work Boots

Price: $1,750
Color: Denim
Brand: Tom Ford
Tom Ford Leather Patch Work Boots
photo source: eBay

The Tom Ford Leather Patch Work Boots were made by the luxury clothing manufacturer from denim and leather piping. They may not be what you immediately think of as work boots, but these women’s shoes are sturdy enough to function in a work setting as well as fashionable enough to be worn for style only.

These boots by Tom Ford can be sold online at auctions for as much as $1,750.

Did you know?

Tom Ford is a private fashion company, one of the newest in its value bracket around, founded in 2005 by Ford. Ford got his start as Gucci’s creative director and moved to his eponymous retail brand with Domenico de Sole, making beauty products and sunglasses.

He debuted his women’s fashion line in 2010, featuring Beyonce, Julianne Moore, Rita Wilson, and more adorned in his glittering new ideas.


5. Men’s Wolverine x Halo: The Master Chief Boot

Price: $1,989
Color: Green
Brand: Wolverine
Men’s Wolverine x Halo: The Master Chief Boot
photo source: eBay

The Men’s Wolverine x Halo: The Master Chief Boot is a brand collaboration between Wolverine and the video game series, Halo. These boots are designed to look like fictional military boots so well that they could be used as work boots if you don’t mind getting their collectible green and gray leather material dirty.

These work boots have rubber outsoles, leather uppers, and a steel-toe structure, giving the wearer real-world protection from injury. They were limited to 117 pairs globally, making them valuable collector’s items. They can sell online for up to $1,989.

Did you know?

Wolverine is a leather boot manufacturer that has been around since 1883, founded by G.A. Krause in Michigan. By the early 1900s, they were crafting 300 boots per day, built for endurance and work-related purposes.


4. PA State Penitentiary Men’s Boots

Price: $2,025
Color: Tan
Brand: &Work
PA State Penitentiary Men’s Boots
photo source: eBay

These lace-up leather boots were made from handmade brown leather for an employee of the PA State Penitentiary. Handmade leather like this is made for functionality and durability, especially in the snow. State boots don’t normally go up for sale, so these shoes sold for $2,025 on eBay despite being heavily worn.

Hand-sewn leather requires using rubber cement to fasten the leather, working a groove into the leather, marking the stitch spacing, using a stitching awl, and starting and locking each stitch. It’s a painstaking process that can only be done by hand and always increases the price of clothes that employ it.

Did you know?

The PA State Penitentiary that these boots came from was opened from 1829 to 1971. It was famous for pioneering separate incarceration systems that prioritized prisoner reformation over corporal punishment.


3. Men’s Red Wing Brown Tan Leather Work Boots

Price: $2,080.48
Color: Brown
Brand: Red Wing
Men’s Red Wing Brown Tan Leather Work Boots
photo source: eBay

The Men’s Red Wing Tan Leather Steel Toe Work Boots listed on eBay are vintage boots from the 1960s made by Red Wing Shoes. The uppers are brown leather with steel toes, which are made for protective reinforcement to protect the user from work-related injuries caused by falling objects or compression.

Instead of steel toes, the same protection can be achieved with a composite material, aluminum, or plastic. Sometimes, steel-toe work boots are required by insurance companies, especially in construction or chemical processing industries. These vintage boots are on sale for $2,080.48.

Did you know?

Red Wing Shoes is a shoe brand that was founded by Charles H. Beckman in 1905, making them one of the oldest clothing manufacturers on this list. They were making over 200,000 pairs of these boots within the first decade of their founding. But they really took off during WWII when they made leather work boots for American soldiers.


2. Custom Monogrammed Alligator Leather Work Boots

Price: $2,159.99
Color: Brown
Brand: Handmade
Custom Monogrammed Alligator Leather Work Boots
photo source: eBay

The Custom Monogrammed Alligator Leather Work Boots are a size 10.5. The custom-made boots are handmade alligator pattern boots with a medium width, made in the old-fashioned cowboy style but constructed for modern rugged work.

They’re pre-owned but vintage, from an unknown year. A seller currently has them listed on eBay for $2,159.99, making them one of the most expensive pairs of work boots available.

Did you know?

Alligator leather is tanned to preserve the leather’s natural durability and enamel sheen. It’s frequently used in luxury clothing, furniture, and even sports equipment because of how strong and pretty it is.


1. Twist Leather Boot

Price: $2,220
Color: Brown
Brand: Berluti
Twist Leather Boot
photo source: Berluti

The most expensive work boots are the Twist Leather Boots. The fashion brand Berluti made these boots from Venezia leather using a method known as incollato construction. Made in the Stefano Bi factory outside Ferrara, Italy, this construction method (incollato or literally, “stuck”) means the shoe’s upper material is folded underneath and sewn to the shoe sole directly.

The Berluti work boots, which have a black lining, a padded insole, and a rubber outsole, were made in Italy for the Winter of 2021 but designed in France. They now retail for $2,220.

Did you know?

Venezia is a patinable calf leather that’s important to keep clean. Despite these boots being sturdy enough to be used as work boots, they should be rubbed with a soft cloth and waxed to maintain the leather.

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