The 5 Worst Boots Men Can Buy

I rarely post super negative reviews of a boot, mostly because I do enough research I buy to make sure I’m paying for boots that I won’t hate, at least.

But after many, many years of working with high-end and not-so-high-end footwear, I wanted to share my least favorite ones — and to make it a super-ultimate-best list of worst boots, I teamed up with another guy who reviews boots for a living.

Weston Kay is a leather worker and the founder of Rose Anvil, a tremendous YouTube channel that became well known for literally dissecting the industry’s best known boots. He, too, knows the sting of disappointment.

The two of us together have worn and reviewed hundreds of boots at this point. These ones are bad!

1. Carhartt

• Glued together with low-quality leather and foam
• They leverage a trusted brand name to sell crappy boots

Let’s get one thing straight: Carhartt makes great workwear. Their jackets, pants, and overalls are all solid, durable, functional, and trusted by tradespeople for generations. But their boots? Absolutely not. Carhartt boots are terrible.

“I’ve cut a few apart, and what’s inside tells the story: synthetic linings, flimsy foam layers, fake printed leather uppers, and soles stacked with cheap materials,” says Weston. “Even the composite toe models, which are styled like rugged work boots, are just cleverly disguised layers of low-quality foam with an injection-molded rubber outsole slapped on. It’s all glued together, not built to last.”

They’re sold as work boots, but they’re just cheap boots with a Carhartt logo on them. The company leans on its hard-earned reputation for quality gear to sell subpar footwear. In Weston’s opinion, that’s misleading.

If you’re buying work boots, you’re probably looking for something that will stand up to long days and tough conditions. These won’t.

What’s especially disappointing is that Carhartt usually avoids synthetic junk in their other gear. Their jackets use heavyweight duck canvas, real cotton, proper hardware — materials that hold up to actual labor.

But that commitment doesn’t extend to their boots. Why? Because they don’t make them. They license the brand out, slap the Carhartt name on generic designs, and call it a day.

2. Dr Martens

• Thin leather that’s prone to cracking
• Practically impossible to resole, despite suggesting otherwise
• No half sizes and a terrible fit
• No leather underfoot

Doc Martens has a committed fan base. When I did a negative review, called Why I Don’t Wear Doc Martens, I was swept off my feet by the deluge of angry comments, but look: I stand by it. They’re bad boots, and I’m saying that despite the fact that a burgundy pair I got at age 17 was my first ever boot purchase.

To be fair, Docs are inexpensive — it would be unfair to hold them to the standards of luxury footwear. And I get that there’s no substitute for their cultural cachet, but once you look past that, you’re left with cheap materials and poor construction. Even though they’re cheap, they’re not a good buy.

“The leather is awful: thin, plasticky, super chrome-tanned, and cheap,” says Weston. “It’s not the kind of leather that patinas well over time. It just won’t age like real leather should.”

Worse still, Docs are a nightmare to resole. This really sticks in my craw because they’re labeled as made with Goodyear welt construction, which usually means it’s easy to resole. But the combination of using a synthetic welt and melting it onto the outsole means most cobblers will refuse the job. And if they do accept it, it’ll be a lot more expensive than a regular resole because replacing the sole involves cutting through glued components that can easily tear. It’s technically doable, but it’s such a hassle that they usually won’t bother.

Even the “Made in England” line, supposedly their premium tier, isn’t that impressive.

“I’ve cut one open,” says Weston. “Under the insole, it’s just fiberboard and foam. The standard 1460 is even worse, just layers of basic foam underfoot. There’s no leather underfoot, so you won’t get the same worn in comfort that many guys look forward to when they buy good boots.”

Also there are no half sizes, they have no shank for stability, they symbolize Cool Britannia but they’re made in Asia… look, I just don’t like them. But the sole is super soft and comfy for a boot, so I’ll give them that: they’ll feel more familiar to guys who are more accustomed to sneakers.

3. Brunt

• Fine for light work, but advertised as suitable for seriously heavy duty work — they aren’t tough enough
• Cemented construction, fake Goodyear welt, and fiberboard insoles

Costing under $150, Brunt are cheap boots, plain and simple. I don’t expect premium materials or construction at that price, and you could argue the boots are fine for the money.

What bugs me is the marketing. Brunt sells them as high-quality, dependable work boots built for serious work, but they’re not. The construction is basic cemented build, a fiberboard insole, a fake Goodyear welt glued onto the upper; it’s all smoke and mirrors.

Nothing about this boot says durability or long-term performance. And yet, they’re being sold to people who need reliability on the job. That’s what gets under my skin.

I’ll admit this one’s a little embarrassing because I featured these in a waterproof boots roundup. In my defense, they are waterproof, and they meet a couple of OSHA standards, and they’re relatively affordable. So at first glance, I thought: “Alright, not bad for the price.”

And they aren’t. They just shouldn’t sell them as boots for the toughest dudes on the job site.

“While they may be functional enough to meet some basic requirements, the marketing overreaches,” says Weston. “These boots are sold as tough, job-site-ready footwear, but they’re not built like it. And that disconnect really frustrates me.”

4. L.L. Bean Boots

• I have no real beef with Bean Boots, I just think they’re ugly
• It’s waterproof and decently constructed

Alright, this entry is tongue in cheek. The classic LL Bean boot is well priced for an American made boot and it lives up to its reputation as a durable, waterproof boot.

I just think it’s ugly.

Every time it rains in New York, everyone is wearing their Bean Boots, and I just want to tell them: you don’t need a waterproof boot to handle rain. Get a nice Goodyear welted boot! You can’t stand in a puddle fishing in them, but they’re more than sufficient for a rainy day in the city. You can buy nicer boots!

“But they’re made in the U.S., the leather is decent, and once you’ve worn through the sole, you can send them back to L.L. Bean,” says Weston. “They’ll replace the entire rubber bottom and stitch the upper back on.”

That’s actually pretty cool. Most cobblers can’t resole them, but L.L. Bean will. Credit where it’s due.

I’m not going to yell at anyone on the street for wearing Bean Boots. I just see them as a symbol of people not knowing how much better their boots could be.

5. Harley-Davidson

• Synthetic linings, crappy leather, and floppy foam
• Another example of a well known brand just sticking a logo on a pair of crappy boots
• Side zips are unnecessary and may blow out

Last up: Harley-Davidson boots. Almost always, if a brand comes out with boots but they’re known for anything other than boots, it means they won’t be great. They’ve contracted the boot making to an external company and they’re just interested in cashing in on the brand name and maximizing profit while they do it.. And Harley is one of the worst offenders.

“We looked at one of their moc toe boots, it was everything I dislike in a boot,” says Weston. “Sloppy interior construction, synthetic linings, floppy materials that shift with each step. The whole thing felt cheap and poorly made.”

It’s meant to be a motorcycle boot, but these are for people who want the logo, not the performance.

“And then there’s the zipper,” says Weston. “I almost always hate zippers on boots, especially when the boot already has speed hooks. It’s unnecessary, and in this case, it adds nothing but more failure points.”

Wrapping Up

And that’s our thoroughly silly, and slightly brutal, roundup of our least favorite boots. If there’s one takeaway from this video, it’s this: when a company that isn’t known for making boots suddenly starts making boots, there’s a good chance they’re not interested in making them well.

And if a boot sounds too good to be true for the price? It probably is.

If you haven’t already, make sure to subscribe to Rose Anvil on YouTube. He’s spectacular — analytical, precise, brutally honest — and not every brand loves that. But we sure do.