10 Work Boots as Stylish as They Are Sturdy

Who said strength and style have to be mutually exclusive? Today, some of the most iconic, classic names in footwear also happen to make some of the best-looking, most stylish work boots on the market—the type of kicks that are as durable as they are dapper. Whether you spend your days working on a job site or at a website, these are sure to do the trick.

Brown leather work boots with yellow laces. photo

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Red Wing 875

Boasting a classic moc toe, a thick rubber sole, and Goodyear welted construction, the Red Wing 875 is a stalwart that blends both form and function. The slightly squared-off moc toe makes them a bit less formal and more hardworking than other boot styles, but the high-quality leather and classic design (they were first made back in the 1950s) help make them a solid everyday shoe. ($280; redwingheritage.com)

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Dark brown men's work boot with black laces photo

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Chippewa Service Boot

Handmade in the USA and boasting full leather welts along with comfort insert insoles, Chippewa's boots evoke the timeless style of WWII era soldiers while providing sturdy construction and enough padding to get you comfortably through whatever battles the day throws at you. ($223; huckberry.com)

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Medium brown men's work boot with brown laces photo

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Alden 405 "Indy Boot"

Pop quiz: Why is the Alden 405 often referred to as the "Indy" boot? Well, because it's the exact model sported onscreen by Indiana Jones. As if that weren't endorsement enough, the Indy boasts a timeless design, Horween leather, and a tempered steel shank that provides both support and comfort while you're hunting down your personal Holy Grail: Happy Hour. ($565; theshoemart.com)

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Black work boot with yellow-orange laces photo

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Thorogood 6" Soft Moc Toe

You don't often hear the phrase "safety toe" used in reference to stylish menswear, but the Thorogoods combine heavy-duty durability with head-turning style. The tobacco oil-tanned leather looks as good in the office as it does on the job site, and the cushioned insole means your feet won't be sore after a 12-hour day. ($163; revzilla.com)

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Black work boots with dark orange laces photo

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Sorel Madson Moc Toe Boot

The Madsons combine the casual style of a moc with a sturdy molded rubber outsole into a boot that looks both heavy duty and hip. Sorel made its name making durable winter boots, meaning the Madsons don't just look good—they'll help keep your feet high and dry through anything Mother Nature throws your way. ($180; sorel.com)

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Classic wheat-colored Timberlands photo

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Timberland Premium Boot

Timberland's flagship boot has become iconic for a reason. Designed more than 40 years ago, these boots have a rounded toe shape that looks as good at work as it does on the weekend. Plus, premium leather uppers and a seam-sealed construction are sure to keep your feet dry, while 400 grams of the company's PrimaLoft insulation are guaranteed to keep them warm. ($190; timberland.com)

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Dark brown laceless boots photo

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Blundstone Chelsea Super 550

Known for its combination of form and function, the Australia-based Blundstone company's iconic Chelsea has been a staple of many men's wardrobes for decades. The 550 model takes its classic Chelsea design and dials everything up to 11, making for a boot that's far more comfortable and durable than the original, but just as stylish. ($190; blundstone.com)

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Black formal-looking men's boots with black laces. photo

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Wolverine Jensen Cap Toe Boot

With the classic style of a cap toe and the hearty construction that Wolverine's become known for, no boot on the planet combines form and function quite as well as the Jensen. The Gore-Tex waterproof lining keeps the water out, while a retro rubber outsole styled after a Wolverine boot from the 1950s provides a strong grip, and the cap toe caps off (forgive me) the look with suit-worthy style. ($225; wolverine.com)

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Black work boots with black leather laces. photo

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Frye Rainer Workboot

Like a lot of the boots on the market, the Rainers boast a moc toe, heavy duty construction, and a rubber outsole for maximum comfort and durability. But unlike the other options you may come across, they come in a handsome waxed Italian suede that offers a different—and arguably more stylish—take on the classic work boot. ($170; nordstromrack.com)

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Dogwood brown boots with matching laces and cream-colored sole. photo

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Caterpillar Chronicle Boot

You'd expect Caterpillar—the machinery company whose construction equipment can be found on almost every job site in America—to make sturdy, no-nonsense boots that can hold up under even the toughest conditions. But you might not expect them to look this good. With a classic round toe shape and full grain leather uppers, the Chronicles lean a little more casual than some of the other work boots on the market, but can look just as good off the job as they perform on it. ($100; catfootwear.com)

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