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These 20 Stylish Chelsea Boots Will Elevate Your Fall Footwear

Over the last few years, Chelsea boots have risen significantly in popularity in the men’s shoe department — and for good reason. The highly versatile men’s boot looks good on its own and pairs well with nearly every outfit you can imagine. Whether you’re rocking a turtleneck sweater and jeans look for fall or need a semi-formal shoe to rock at a work function — the Chelsea boot is there for you. Plus, they tend to be built durably and can handle the elements throughout fall and winter, so your feet will stay warm, dry and stylish at the same time.

After the creation of the Chelsea boot in 1851, it became the British equivalent of a cowboy boot and gained a second life thanks to the Beatles.

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The boots are still the same now as they were then: made of lighter materials, an elastic center, and a pull tab that makes the boots slip on and off with ease. Whether it’s full suede, leather, or rubber, we’ve rounded up 17 of our favorite Chelsea boots on the market. Whether you’re a leather fanatic, a classic dresser or someone who loves to make a statement — there’s a Chelsea boot in this list that will fit your fancy.

Read More: The Best Boot Socks


1. Thursday Boot Company Duke Chelsea Boots


Thursday Boot Company is one of those direct-to-consumer brands that’s gained considerable popularity in recent years — but don’t let fancy Instagram ads get to you, as they’re capable of making extremely quality products. Their take on a Chelsea-style boot, known as the Duke, is our pick for the best Chelsea boot around. The moldable footbed contours to your foot over time, the suede itself is water-resistant (should you get caught in the rain), and the footbed has plenty of good traction. While we like the versatility of the Dark Olive suede, there are plenty of other colors.

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Courtesy of Amazon


2. Blundstone Lug Chelsea Boot


We’re huge fans of Blundstone Chelsea Boots. Made to last for at least five years, they’re stylish, well-made and comfortable. We covered their latest release, and this new Blundstone Chelsea boot changes everything. The lug sole’s design makes it appear like a swooshing wave. It’s a high-fashion touch to a functional boot.

Read More: Is the New Blundstone Boot Collection Too Fancy?

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Courtesy of Blundstone

3. Banana Republic Factory Suede Chelsea Boot


We’re all watching our pennies these days, so when a cool pair of Chelsea boots go on sale, you grab them. This suede Chelsea boot comes in two colors, has a back tab and rests on a rubber outsole.

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Courtesy of Banana Republic



4. Amberjack Chelsea Boot


Amberjack designs their footwear with the aim of uncompromising comfort and up-to-the-minute styles. They want you to forget that you’re wearing shoes. Their contemporary-styled Chelsea boot comes in leather or suede. Shown here in black, they also have buttery lemon suede and other colors that can brighten up a wardrobe.

Their Italian suede is water repellent and sourced from Tuscany. The Chelsea boot has heat-activated arch support, a dual-density outsole that’s flexible in front, and hiking boot material in the back. The boots are lined in perforated sheepskin.

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Courtesy of Amberjack

5. Allen Edmonds Liverpool Chelsea Dress Boot


Established in 1922, Allen Edmonds footwear, each pair is worked on by 48 different people completing 212 steps before the shoe ends in the shoe box. Known for their exemplary dress shoes, they’ve gone forward and created equally snazzy sneakers and boots.

This Chelsea boot comes in many widths, from B to EEE. Loosely based on the Jodhpur (short-riding boot), this boot has a 360-degree bench welt construction. It’s lined in leather with the brand’s CustomCork insoles that mold to your foot. The uppers are made from European calfskin leather, while the soles are vegetable-tanned leather with treads at the forefoot and toe for traction.  This Chelsea boot also comes in dark brown and black.

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Courtesy of Allen Edmonds



6. Kenneth Cole Liam Chelsea Sneaker


Kenneth Cole started as a footwear company in the early 1980s and expanded to clothing and accessories. From its start, the company has always been committed to social causes and has partnered with nonprofits.

Their Chelsea boot is the very best amalgam of boot and sneaker. It retains the Chelsea boot shaft and vamp but rests on a sneaker outsole. The midsole is triple-layered, flexible, and feels like pillows for your feet. The Liam also comes in black. Try it with jeans or chinos.

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Courtesy of Kenneth Cole

7. R.M. Williams Craftsman Leather Chelsea Boots


Another great R.M. Williams option, this leather Craftsman boot is made by some of Australia’s best, and it shows. The company’s head of production, Mr. Michael Williams, has been with the company since he was an apprentice 40 years ago and says these boots are his favorite. The block heels give a little lift and, according to Williams, once “you break in a ‘Craftsman,’ and the leather then starts forming to your foot, I find them so comfortable.” Take it from him and grab a pair. If you want leather, there’s no better pair.

Read More: Best Leather Boots For Men

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Courtesy of R.M. Williams


8. Camper Pix Boot


Camper shoes are known for their individuality. Styles are slightly tweaked to stand out from the herd. Take their Chelsea boot. The boot sits on grooved EVA outsoles, designed with Tencel Lyocell uppers in a subtle shadow stripe. The lining is constructed with recycled materials. There’s an Ortholite insole for cushioning and shock absorption. They come with a two-year guarantee.

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Courtesy of Camper

9. Belstaff Trialmaster Leather Boots


The company known for its ridiculously gorgeous motorcycle jackets makes equally delicious footwear. This boot is based on one of the heritage designs that Che Guevara and Steve McQueen wore. Stylistically, it’s a blend of jodhpur and Chelsea with the addition of buckled straps festooning the vamp and heel back. One look at this Chelsea boot, and you can hear engines roar.

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Courtesy of Mr Porter


10. Crown Vintage Glory 2 Chelsea Boots


Crown Vintage is DSW’s footwear brand. They don’t skimp on construction or style. Their Chelsea boot’s upper is suede with a leather gusset and striped back strap. It has a removable EVA Ortholite insole, rubber midsole, and rubber sole. Concerned about possible water damage? Check out these products that waterproof suede.

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Courtesy of DSW


11. Blundstone Chelsea Boot


Decidedly workwear in their look and structure, Blundstones are a rough and tough pair of boots. Expertly made to look as utilitarian as possible, Blundstones are chunky — but stylishly. Originating from Australia, they’re seemingly a distant cousin of something like Red Wings or other similar heritage boots. The smokey black color is also a nice change of pace from your typical black leather boot. 

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Courtesy of Amazon


12. Bearpaw Nick Boot


These suede Chelsea boots are treated with the brand’s neverwet technology (liquids roll off the suede), have a canvas lining, and comfort sheepskin footbed. Not only will your feet be toasty warm and stylish, but the rubber outsole prevents slipping.  Wear these rugged Chelsea Boots after a day on the slopes or every day.

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Courtesy of DSW

13. Thursday Boot Company Legend Black Matte Boots


There’s something about matte that’s just so… sophisticated and classy. The black matte surface on the outside comes from their Rugged and Resilient leather with a Goodyear Welt Construction for durability. These boots also have cork-bed midsoles that form to your feet the more you wear them for comfort. They’re handcrafted and built for men who wear their boots out until they’re on their last leg, so there’s no need to treat them gently.

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Courtesy of Thursday Boot Co.


14. Hunter Original Waterproof Chelsea Boot


If you love the style and shape of a Chelsea boot but want something you can wear in the rain without worrying about ruining it, Hunter’s “Original” Chelsea boot can withstand all kinds of nasty weather. A strong rubber sole provides traction and grip; you won’t slip and slide while walking along. While it’s great to wear as a commuting shoe when there’s a torrential downpour, they work just as well in the sun for those looking to play with textures in their outfit.

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Courtesy of Nordstrom


15. Sperry Cold Bay Rubber Chelsea Boot


You knew that Sperry made boat shoes and sneakers, but did you know they also made boots? Sperry makes hiking, duck, deck and Chelsea boots. Sperry’s Chelsea boots are made specifically to handle rain and stormy weather. This Chelsea boot is made with a waterproof shell, lined in microfleece and a rubber lug outsole with Sperry’s molded Wave-Swiping for added traction.

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Courtesy of Sperry

16. Xtratuf Legacy Leather Chelsea Boot


Initially created for the men and women who work on land and sea in Alaska, Xtratuf boots are meant to be worn no matter how wretched the outdoors are or how crazy the wind, rain and snow get. And like any brand built for durability and warmth, non-fishermen have jumped on owning performance-tested footwear, even if they aren’t living in the tundra.

Their Chelsea boot is made with saltwater-resistant leather and is 100% waterproof. Sporty looking, it has a non-marking outsole and is SRA-rated slip-resistant. It’s lightweight and can be worn on and off boats. Yes, it’s perfectly fine to wear them on city streets or country roads. This Chelsea boot is also acid and chemical-resistant. In other words, no matter what you do to this boot, it will always look great.

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Courtesy of Xtratuf

17. Dr. Martens Chelsea Boot


Relevant now just as much now as they were back in the 1980s, the Doc Martens silhouette has been a classic style shoe that’s just as beloved by punks as by fashionistas. The rugged, rubber sole is instantly recognizable, giving a slight military-inspired vibe to whatever other clothing you pair alongside them. Plus, as a Chelsea-style boot, they’re easy to take on and off and durable enough to wear repeatedly.

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Courtesy of Amazon

18. Chaco Revel Chelsea Boot


Cozy as sitting by the fire during the winter, Chaco’s Chelsea boot is both a slipper and an outdoor shoe.  It has a comfortable, felted polyester upper and a crepe-textured lug outsole. The elastic gore makes getting it on and off a breeze. Inside, the boot is lined in fleece, and the podiatrist-approved removable arch support is great for long walks. Even in the snow.  It also comes in gray, brown and black.

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Courtesy of Nordstrom

19. Deer Stags Rockland Chelsea Boot


With almost 5,000 five-star reviews, many guys dig Deer Stags Chelsea boot. The cleanly designed boot has a faux leather upper and a rubber TPR outsole. Inside the boot is all about comfort. Lined in fabric, it has a removable memory foam inner sole. It also comes in black.

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Courtesy of Amazon

20. UGG Biltmore Chelsea Boot


Ruggedly handsome, this UGG Chelsea boot is crafted with the same well-thought-out designs as their world-famous Uggs. The waterproof leather upper has a wide elastic gore on the sides, enabling ease of getting a foot in and out of the boot. It has seam-sealed construction and a hollow core outsole, so they feel light on the feet. And to prevent slippage, UGG uses White Spider rubber that keeps its traction working, even when it’s freezing out.

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Courtesy of Amazon