The Best Rockstar-Inspired Leather Boots to Buy Right Now

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Leather boots might be the most ubiquitous footwear on the planet. What other pair of shoes are worn by runway models, ranchers and rockstars alike? Of course, the best leather boots might be different depending on your occupation and personal style, but one thing’s for sure: every guy deserves a great pair of leather boots.

This universality of leather boots wasn’t always a thing. As with so many fashion staples, the rise of modern leather boots in fashion really started with the counterculture movement of the sixties and seventies. Before then, leather boots were exclusively for working men. Then came the style pioneers: Early rockstars such as The Beatles, alongside Hollywood legends like Marlon Brando, started wearing leather boots with fresh, rebellious fits. And, as expected, young people ate it up. Chelsea boots were even colloquially renamed “Beatle boots” after Paul McCartney and John Lennon added the Cuban heel to old slip-on leather boot.

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Leather boots were later solidified as a rebellious statement in the eighties with punk rockers wearing Dr. Martens and similar combat boots (see: The Clash). Today, the leather boot trend is alive and well thanks to cultural icons from Harry Styles to Lenny Kravitz. In other words, there’s never been a better time to boot up.

Leather Boot Buying Guide

There’s a lot to choose from when picking the best leather boots. A good place to start is deciding how you’ll be wearing your new boots. Will you be rocking them in bad weather? Will they ever be used as work boots? Or are they for the office and date nights? Below are a few other considerations to keep in mind while shopping for the best leather boots online.

Style: Although leather boots come in dozens of styles, we’ve narrowed it down to three categories: Chelsea boots, western/cowboy boots and lace-ups (i.e. brogues or combat boots).

Chelsea boots are elasticated slip-ons popularized by mid-century rockstars, and they make an excellent choice for nights out or office attire (as they aren’t too casual or too dressy).

Western boots should be familiar – especially now, as the cowboy look continues its trendiness.

Lace-ups come in a few forms, including old-school brogues, traditional work boots and combat boots (Dr. Martens, for example).

Nowadays, almost all styles of leather boots are acceptable for everyday wear. Generally speaking though, Chelsea boots are best for more fashion-forward, dressier occasions, while cowboy boots are great for bold outfits (unless you’re an actual cowboy) and lace-ups are more casual.

Build Quality: The best leather boots are built to last. Look out for premium leather (full-grain is the highest quality), handmade construction and brands with a reputation for craftsmanship.

Waterproofing: Durable leather boots can be great in the rain and snow, but others (such as suede Chelseas) should not touch water. Make sure to check out a boot’s water-resistance – if any – before buying.

What Are the Best Leather Boots to Buy Online?

The best leather boots can make a strong style statement but they’re also investment pieces that you can wear in beautifully over time. We rounded up ten pairs of leather boots for men that are worth your money and attention.

1. Saint Laurent Wyatt Chelsea Boots

Saint Laurent’s Wyatt Chelsea boots are about as rock ‘n’ roll as fashion gets in the 21st century. The Wyatt boot was a leading piece in Hedi Slimane’s edgy revamp of Saint Laurent back in 2013, and, after becoming an instant hit, stylish people are still saving up for the boots today.

This is largely due to the Wyatt’s near-perfect design (a four-inch heel, leather sole and clean lines at every angle), but the boots’ success is also due to their impeccable calfskin build and Italian craftsmanship. They’ll just get better with age, and, at this point, we’re pretty sure they’ll outlast almost any trend that comes around.

Courtesy Ssense

Buy:Saint Laurent Wyatt Chelsea Bootsat$895.00

2. Dr. Martens 1460

Dr. Martens boots were the essential part of any punk uniform in the seventies and eighties. Recently, they’ve come roaring back into style with cameos on the feet of everyone from Pharrell to Rihanna.

This pair – the 1460 – is Dr. Martens’ most classic model, sporting an eight-eyelet lace-up front and a chunky-as-hell PVC outsole. Since their invention over 70 years ago, the boots have integrated processes such as heat-sealing the sole to ensure a rugged, long-lasting build. Pair the boots with modern punk outfits like black jeans and a leather jacket, or go more low-key with a button-up.


Buy:Dr. Martens 1460at$149.95

3. Common Projects Suede Chelsea Boots

Suede Chelsea boots have been having a moment recently. They’re more casual and easier to wear than regular leather boots, making them a good alternative to sneakers. This pair from Common Projects is a great example of that casual, rock-inspired look that has revitalized the boot style. Although they’re refined enough for the office, these boots are designed for comfort with cushioned rubber-crepe soles, tapered toes and a soft, premium suede material. They’re just as high-quality as you’d expect from an Italian-made boot – which is hinted at by Common Project’s characteristic gold serial numbers on the heel.

Courtesy Mr. Porter

Buy:Common Projects Suede Chelsea Bootsat$525.00

4. John Varvatos Eldridge Harness Boot

John Varvatos made its name by marrying designer fashion and rock ‘n roll, so it’s no surprise that the New York brand makes some badass boots. These motorcycle-slash-Chelsea Eldridge boots are one of our favorites with some distinct yet highly wearable edge. The boots are marked by motorcycle harness straps over the insteps, stacked heels and premium leather. They’re certainly a statement, and we suggest rocking the boots with black jeans and killer leather jacket or slouchy sweater.


Buy:John Varvatos Eldridge Harness Bootat$698.00

5. Filson Service Boots

Filson is a good source for anything rugged enough for the woods and stylish enough for the city. These Service Boots are one such piece from the outdoors brand.

Style-wise, they’re a throwback to early 20th-century military boots with surprising mobility, a lace-up front and a bit of a heel. Despite their old-school charm, the boots are seriously well-made with full-grain leather, Goodyear storm welted soles (for extra water resistance) and triple stitching at stress points. They’re also very capable (if you choose to wear them outdoors) thanks to a grippy Vibram outsole and water resistance throughout. All-in-all, they’re somehow both stylish and tough-as-nails.

Courtesy Filson

Buy:Filson Service Bootsat$368.00

6. Belstaff Trialmaster Leather Boots

Motorcycle boots were some of the first leather boots to become big in fashion – largely thanks to Brando’s movie, The Wild One. These Trialmasters from Belstaff offer that tough style in a boot that’s more low-key and wearable. Still, they’re very capable with hand-waxed calfskin leather that has a water-repellent coating. You can wear them like a biker (leather jacket, black jeans) but you can also rock them with modern pieces as well (say, blue jeans and a cashmere sweater).

Courtesy Mr. Porter

Buy:Belstaff Trialmaster Leather Bootsat$395.00

7. Red Wing Heritage 6″ Moc Toe

Red Wing’s classic work boots made a comeback a few years ago with the hipster trend. But now things have settled down and the rugged boots are being worn by everyone (i.e. not just hipsters). We’re happy about this because Red Wings are truly great boots.

The workwear look is timelessly stylish, and, because they’re made for working, they’re very comfortable and well-made too. On the outside, you’ll find water-repellent full-grain leather, while the inside boasts moisture-wicking properties and a leather footbed that molds to your foot. They’ll last years and look even better with wear.


Buy:Red Wing Heritage 6at$279.99

8. Justin Jackson

If your style inspirations are more country, check out these all-black Justin Jacksons. They’re minimal enough to wear like black leather Chelseas, so you can rock them with almost everything from jeans and a tee to a suit (really). They also come from Justin, an esteemed western bootmaker. Justin has been around since 1879, and the brand has always been a go-to for both actual cowboys and those of us looking to inject some western style into our wardrobe.


Buy:Justin Jacksonat$149.95

9. Off-White Black Hiking Boots

For a rap-rockstar look (à la Lil Uzi Vert or Playboi Carti), check out these hiking boots from Virgil Abloh’s Off-White. They feature some subtle tweaks to the typical hiking boot, including buffed leather, gold-tone logo hardware near the heel and a stacked leather-rubber midsole. But, despite their upgrades, the boots maintain their rugged inspiration for a balanced style. They’re are a modern statement piece through-and-through, and should be worn accordingly with bold looks.

Courtesy Ssense

Buy:Off-White Black Hiking Bootsat$1,225.00

10. Church’s Brogue Detail Boots

Church’s, an English footwear brand founded in 1873, has been a staple of English fashion for over a century. The brand’s iconic blend of dressy and rugged has led their shoes to the feet of prime ministers and Pierce Brosnan’s James Bond alike. These brogues are some of our favorites, oozing upscale rockstar vibes.

As with most great boots, they’re both durable and clean-cut thanks to premium materials and expert craftsmanship (each pair takes about 8-10 weeks to complete by hand). They can be worn casually, but we think they look best more dressed-up with, say a suit and maybe a trench coat.

Courtesy Farfetch

Buy:Church's Brogue Detail Bootsat$750

See more Rolling Stone footwear picks here

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