If you purchase an independently reviewed product or service through a link on our website, SPY.com may receive an affiliate commission.
Men’s leather boots are a staple for any guy’s wardrobe. Whether you live in athleisure almost 24/7 or have to dress up each day to head into the office, there will forever be one of the best men’s boots available in leather to help step up your style.
One of the great things about leather and men’s leather boots, aside from them looking so handsome, is that they’re extremely durable. If you take care of the boots, a great pair of men’s leather boots can last you well over 10 years. This means if you buy a slightly pricier boot and then amortize the cost, that expensive pair of men’s leather boots you’ve been eyeing will realistically cost you next to nothing. Sometimes math is your friend.
We did some searching around and found the twelve most versatile, coolest-looking men’s leather boots to wear now, tomorrow and 10 years down the road. Check out all of our choices below.
1. Thursday Boot Captain Lace-Up Boot
Sustainability and style are two of the reasons we’re huge fans of the Thursday Boot Company. And you may have noticed that we’ve covered them before. One of their standout styles is the Captain. This boot with a six-inch shaft has a stitched-down cap-toe. That one detail elevates these men’s leather boots and lets you wear them with suits or dress pants.
We love these boots so much that we named them the best boots two years running in the 2021 Man, our end-of-year product awards.
2. Red Wing Heritage Men’s Moc 6″ Boot
Red Wing started off as a work boot company, and while they still roll out dozens of those styles, they also offer a fashion line. Their lace-up moc-toed boot is made in the USA. This men’s leather boot is a sturdy work boot, and a great all-around casual boot for everyday wear. Red Wing boots are definitely an investment, but if you care for them properly (and you’re going too, right?), they’re last for years. They’re also a subtle style flex that will earn you compliments and knowing nods wherever you go.
3. Wolverine 1000 Mile Moc-Toe Boot
Over here at SPY, Wolverine and Thursday Boot Company are running neck and neck as our favorite men’s leather boots. One week Wolverine pulls ahead, and the next it’s the Thursday Boot Company. Why is it hard to decide whose boot is better? Because both brands are freaking awesome. Wolverine’s 1000 Mile boots have been on men’s feet for over 100 years and counting. The classic silhouette has consistently delivered style and comfort, and they can go from weekend to biz casual to the great outdoors with ease.
4. Cole Haan 4.ZERØGRAND Explore Boot
BEST FOR HIKING
Cole Haan knows that a stroll can turn into a day-long hike, and that sometimes you need good traction in the city just like you do on the traills. That’s why they made their 4.ZERØGRAND Explore Boots stylish enough for both a night out on the town and a hike through the forest. The men’s leather boot is totally waterproof, making your feet prepared for whatever you might have going on that day. The outsole is not only durable for years of wear but exceptionally lightweight so it doesn’t feel as if you’re lugging bricks around all day. If any leather boots for men can do it all, this is really the one.
5. Bugatchi Ellis Chukka Boot
BEST MODERN CHUKKA
When you think of chukka boots, you probably envision one in an earth-tone suede. Bugatchi takes this classic style and amps it up. Their full-grain calfskin leather chukka gleams with sophistication. The toe has brogue detailing (now you can wear them with more than jeans) and they sit on a single-layer leather sole. Dress ’em up, dress ’em down or maybe mix ’em in an outfit somewhere in the middle.
6. Blundstone Unisex Dress Chelsea Boot
BEST CHELSEA BOOTS
Whether you’re mucking about on city streets, down a trail or actually mucking out farm style, Blundstone’s Chelsea boots have been serving style and durability for years. This classic boot normally goes for a couple of hundred dollars more, so when we spotted it at a reduced price, we had to let you know.
7. Thursday Boots Casa Moto Boots
BEST NEW STYLE
You’re going crazy if you thought we were going to only put one pick from Thursday Boots in here. Like, come on, they’re a SPY favorite. We’re obsessed. The brand-new Casa Moto Boots (made in collaboration with none other than Casamigos) are boldly and joyfully designed in full-grain leather to up your style as we continue on in the season. As we’re used to with Thursday Boots at this point, these puppies have a comfortable cork-bed midsole that forms to your foot. But, one new aspect here is the “Army Track” lug outsole for a powerful grip that won’t go unnoticed.
Right now, you can get these boots in three different colors ranging from size 6 to 16, but if we’ve learned anything from Thursday Boots over the years, these are probably going to sell out sooner rather than later.
8. Dr. Martens 1460 Smooth Leather Lace Up Boots
Ah, Doc Martens. How could you go wrong with the classics? Whether these were the boots you wore to rebel against your parents in your punk 90s phase or the pair that made you feel ever so slightly edgier in your 2010 Tumblr era, Dr. Martens leather boots have been there through it all. They’ve got a timeless look to them that feels instantly recognizable due to the chunky look and classic yellow details throughout. Although it’s a look that you might feel is a little bit out of style, trust us. These babies will never go out of style.
9. L.L.Bean Bean Boots
BEST DUCK BOOTS
The Bean Boots! These infamous duck boots coined the term “duck boots” and are singlehandedly the best duck boots of all time. L.L.Bean himself (founder Leon Leonwood Bean, duh) created these boots back in 1912 where soon after they became a necessity for hunters. Although they’re still used for hunting and other outdoor escapades in 2022, these are also great to add to your everyday style.
Read More: Our Favorite Duck Boots for 2022
10. Florsheim Duke Boot
The leather sourced for these men’s leather boots comes from tanneries that have either a gold or silver rating from the Leather Working Group. Florsheim’s serious when it comes to delivering a style that doesn’t hurt Mother Nature. This bike toe boot is all sleek minimalism and modern style.
11. Vagabond Jeff Boots
The Chelsea boot style is one of the most versatile men’s leather boot styles around. Raise the boot just a little bit and it’s all “looks like I have a fashion degree, doesn’t it?” vibes. Sleekly created as an updated, chunkier look to the classic Chelsea boot, the Jeff Boot from Vagabond will bring your style up a couple of notches. Essentially, these are the Chelsea boots of 2022.
12. Rossignol 1907 Chamonix Buffalo Brown Boots
Rossignol’s footwear is as every bit as functionally chic as their ski wear. This men’s leather boot is modeled on their classic hiking boot. This one is waterproof and insulated. No matter what the weather, this on-trend boot protects your feet. And it’s snazzy-looking too.