the greatest gift

What Are the Best Work Boots for Men to Give?

Our winner: The Red Wing 875s. Photo: Courtesy of the retailer

Where can you find the nicest scarf? Who makes the best cashmere sweater? Every year around this time — like holiday classics on the radio — certain gifts become popular all over again. To determine the very best versions of those things, we’re talking to experts, adding our own opinions, and even testing products ourselves to find the greatest gift (plus several runners-up).

Given that most people don’t use them to work, it’s a little hard to describe a “work boot,” but the ones we have in mind should conjure an image of a traditionally made rugged leather boot, similar to what carpenters or construction workers relied on in the early-to-mid 1900s. They have a thick rubber sole, a wide toe, and usually at least six pairs of eyelets. Even today, these so-called heritage boots are plenty tough and look good with almost any kind of outfit.

To find the best work boots for men, I set my sights on those that are the most comfortable, stylish, and built to last the longest. I consulted experts from men’s style writers and retailers and also considered my own experience as a work-boot enthusiast. Ultimately, one pair of work boots rose above the others. Don’t miss all of the Strategist’s holiday gift coverage right here, too.

The best work boot

Often when I called experts to ask about the best work boots, my question would be met with silence until I said, “You know, something like the Red Wing 875.” A category definer, Red Wing boots have been around since 1905, making it one of the oldest and best-known work-boot companies still manufacturing in the U.S.

The 875 is the gold-standard work boot — it’s the only pair owned by all three members of my expert panel. It’s by no means inexpensive, but you get a boot that can easily last ten years or much longer if properly cared for. Adam Levy, co-owner of renowned workwear retailer Dave’s New York, says the 875 is a consistent best seller, and has a little something for everyone. “It’s a crossover from work to style and it has been for decades. Used by carpenters, farmers, electricians and ironworkers, it’s a staple of the work trade, but also our most popular style for the casual wearer.”

I have to confess: I have a pair of Red Wings 875s myself. I got them second-hand; they were probably at least a few years old, in pretty good condition besides some frayed laces and completely worn-down soles. I sent them into Red Wing and three weeks later received my basically good-as-new boots. That’s my favorite thing about Red Wing, and another reason they get our top spot — the company offers repair services on all of their products. For $125, you get a full-service reconditioning, or you can pay $100 to just replace the sole. Resoling saves you from buying new boots every few years, and it means you can keep your broken-in pair as long as possible.


The Chippewa Service Boot was another popular choice among the experts. Established in 1901 and still producing in the U.S., Chippewa is one of the few companies that can compete with Red Wing for Americana cred. The Service Boot’s profile is cleaner and more slimmed-down than the 875 and most other work boots, so it’s easier to dress up, too. Despite the more refined look, it’s still a tough boot. “You can beat the hell out of them and they just get better and better,” says Brian Davis, owner of vintage menswear specialist Wooden Sleepers in Brooklyn. Davis has been going strong with his pair for a few years and counting.

One drawback is that Chippewa doesn’t offer recrafting services in-house, but since it’s a Goodyear-welted sole, any good cobbler should be able to replace it. You can also try shipping the boots to a company like NuShoe that specializes in resoling and recrafting.

Another Red Wing boot. Similar to the Chippewa Service Boot, the Iron Ranger’s easy to dress up or down. It’s a little more stylized compared to the 875, with contrast stitching along the toe and sides. According to Red Wing, the boot was originally made for iron miners in the early 1900s — hence the name. The boot’s signature “double-layered” toe was intended to “protect the miner’s feet.” Adam Levy of Dave’s says, “This is one of those boots that take a while to break in, but once they do, they become your favorite pair.”

The Alden “Indy” Boot is a bit of legend in the work-boot world. Its origin story, repeated on menswear chat forums and blogs, is that Harrison Ford, on the set of Indiana Jones, insisted on wearing his own Alden boots, which were immortalized onscreen and forever dubbed “Indy Boots.” I spoke with men’s style writer Josh Sims, author of The Icons of Men’s Style, who adds, “I’m told that the costume designer had suggested Red Wings, but Harrison wore Aldens for his carpentry, and so it was Alden that got to cash in.” Aside from the Harrison Ford connection, Alden is one of the most trusted names in American footwear, founded in 1884 in Massachusetts, where the company still manufactures. Sims says it’s the work boot that’s “easy to polish up,” as the Indy combines the durability and spirit of a work boot with the more streamlined look of a dress boot.

The Timberland Pro Boondock is a work boot for actual work. This thing is a tank. It’s not as able to easily cross over into casual wear like the other options, but if you need a solid, reliable work boot with all the right features, this is the one. According to Levy, “This one is all function: Waterproof. Composite toe that meets all safety requirements for job sites. Rubber toe cap. Heel guard. Heavy-duty cleated outsole. Anti-fatigue insole. Super durable leather to make it stand up to any job. This is the boot that people in construction wear when they want quality, function, and all the features to keep them comfortable and on the job.”

Levy also recommends this boot from Timberland PRO for a more affordable option that still delivers great quality: “This one takes the look of the classic Timberland and the function of being waterproof and insulated, but it doesn’t have a high price tag.”

I also want to note one more option — though none of the experts specifically mentioned this model, lots of good things have been said online about the Thorogood, especially as a cheaper alternative to the Red Wing boots that took our top spot. They’re also made in the U.S., can be sent back to be resoled by Thorogood, and can be yours for a much better price.

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What Are the Best Work Boots for Men to Give?