Men’s leather boots are a staple for any guy’s wardrobe. Whether you live in athleisure or dress up for work, there’s a men’s boot in leather that will fit your style. One of the great things about leather and men’s leather boots, in general, is that if you take care of the boots, they can last you 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 — after you break down the price/length of wear ratio — will cost you next to nothing. Sometimes math is your friend.
We did some searching around and came up with the 12 most versatile and coolest-looking men’s leather boots to wear now and for the next decade-plus. Our picks below.
1. Thursday Boot Company 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.
2. Wolverine 1000 Mile 1940 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 cassual to the great outdoors with ease.
3. Blundstone Unisex Dress Chelsea Boot
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.
4. Staheekum Redwood Boot
BEST FOR HIKING
Based in the Pacific Northwest, Staheekum gets that a stroll could turn into a day-long hike. Their Redwood lace-up hiking boot is stylish enough for a night out. The men’s leather boot has a contrasting color padded collar, nifty-looking two-tone laces, a molded foam insole (bliss on your feet) and a thick rubber outsole.
5. Bugatchi Verona 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 waxed leather chukka gleams with sophistication. The toe has brogue detailing (now you can wear them with more than jeans) and they sit on a microfiber rubber sole.
6. 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 style that doesn’t hurt Mother Nature. This bike toe boot is all sleek minimalism and modern style.
7. Vagabond Harvey Boots
The Chelsea boot style is one of the most versatile men’s leather boot styles around. Make it in suede and it’s all “weekend and craft beer” vibes. Make it in leather sourced from a Leather Working Group rated tannery, and it’s all “whisky and glittering nights” vibe. Sleekly created, this Chelsea boot does come in other shades, and yes, suede too.
8. Taft Dylan Boot in Beige
BEST AFFORDABLE DESIGNER BRAND
Taft boots are boldly and joyfully designed. Many times, we’ve attempted to add them to a men’s leather boot roundup, only to find out that a few of their styles were temporarily sold out. Right now their updated Jodhpur boot in beige suede is available for purchase. Grab it before someone else does.
9. Naot Limba Boot
BEST WITH OR WITHOUT ORTHOTICS
Naot’s boots all come with a removable cork and latex footbed, so if you need to add an orthotic to your footwear, this pair’s an easy fix. The Limba is a cross between a desert and work boot, casually cool for everyday wear. It’s got a lightweight grippy lug sole, and the boot’s shaft is four inches high.
10. 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.
11. New Republic Ventura Leather Chelsea Boot
The problem with some dress boots is their soles, they’re kinda slippy. New Republic’s upscale-looking Chelsea boot has a grippy rubber outsole, so no matter what terrain you’re trodding, you stay upright. This boot comes in deep chocolate brown or black.
12. Red Wing Heritage Men’s Moc 6″ Boot
BEST FOR WORK OR PLAY
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.