10 Best Chelsea Boots for Men

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The Chelsea boot is a shoe that’s effortless, comfortable and polished.

It continues to trend in men’s fashion thanks to its easy to slip-on design and sleek construction. Whether you prefer suede or leather, the stylish shoe remains one of the most fashionable footwear choices for men, especially in the fall and winter seasons.

With roots in England, the Chelsea boot dates back to the 19th century when royal cordwainer, cobbler J. Sparkes-Hall, created a boot with elasticated sides for Queen Victoria. While originally dubbed “the paddock boot” the silhouette became noteworthy thanks to its slip-on construction and sturdy sole. 

Fast-forward to the 1950s and 1960s when a similar style of boot was worn in the trendy district of Chelsea in London. Young British adults and teenagers began to be spotted in the style and it was dubbed the “Chelsea boot.” The style became synonymous with the mod scene — a youth subculture inspired by modernism that took hold in the U.K. — and eventually the rest of the world by storm. British bands such as The Beatles, The Rolling Stones and The Who adopted the stylish footwear option, giving the Chelsea boot an avenue to enter the mainstream by way of popular musicians.

Today, the polished boot continues to be a style favored by both men and women thanks to its minimal shape, easy-to-put-on construction and sleek silhouette. The boot can instantly elevate a pair of jeans or pants. Additionally, the shoe is lace-less, giving you one less thing to worry about as you go about your day. 

The English boot’s versatility and practicality are key factors that continue to push its relevance on the market. Over time, countless brands from Blundstone to Calvin Klein have adopted the shape, making the classic style their very own.

When looking for the best Chelsea boot for men in 2020, there are a few key factors to consider. The best boots are made with a water-resistant upper, so you can wear your leather or suede shoes rain or shine. Another is a sturdy pull tab, which is what makes the Chelsea boot such a convenient footwear option. Lug soles for traction and cushioned footbeds are other features that make boots worth buying.

Our top ten choices factor in all these qualities and more. Some have even been highly reviewed by thousands of customers on Amazon, so you can trust that you’ll be happy with your purchase.

Below, take a look at the best Chelsea boots for men you can buy in 2020.

Timberland Men’s Stormbuck Chelsea Boot

Comfortable and durable, Timerbland’s Stormbuck Chelsea boot for men top our list. Featuring a waterproof full-grain leather upper, this pair can be worn even when it rains. Plus, the rubber sole is made out of 34% recycled leather, adding a sustainable touch. Available in black or brown, this Chelsea boot can easily be styled with your favorite closet staples year-round; simply slip on and go.

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CREDIT: Courtesy of Timberland

Dr. Martens 2976 Chelsea Boot

The first rendition of the 2976 boot was created by Dr. Martens in the 1970s. Today, it continues to be a customer favorite thanks to its sturdy leather upper and signature chunky rubber lug sole. You can snag a few colorways of the classic shoe that feature Dr. Martens’ iconic logo on the pull tab via Amazon.com. With over 1,000 reviews, users note that you should size down, as Dr. Martens tend to run on the larger side.

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CREDIT: Courtesy of Amazon

Cole Haan Men’s Wakefield Grand Waterproof Chelsea Boot

Take on the rain and cold with Cole Haan’s Wakefield Chelsea boot. The water-resistant leather style comes in a tan option with navy elastic sidings as well as an all-black edition. The suede boot will have you looking stylish without having to compromise comfort thanks to the molded footbed with arch support. All in all, this boot will help keep feet happy even on the rainiest of days.

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CREDIT: Courtesy of Nordstrom

Clarks Paulson Up Leather Chelsea Boots

Comfortable and classic, these black leather Chelsea boots from Clarks are another great option to consider. Available on Nordstromrack.com, reviewers note that the Paulson Up leather Chelsea boot won’t rub on the sides of your foot as some leather shoes can. The versatile option can elevate any look with ease year-round, whether it be for a casual or formal outing.


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CREDIT: Courtesy of Nordstrom Rack

Blundstone Men’s 1911 Boot

Embrace adventure with Blundstone’s rendition of the classic slip-on boot. This suede Chelsea boot has a water-resistant upper, removable footbed and shock-absorbing lug sole that minimizes impact with every step. The utilitarian pair can be worn for a casual hike or while out on the town. Additionally, the 1911 boot from Blundstone for men is equipped with two pull tabs in the front and back, so you can put it on with ease.

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CREDIT: Courtesy of Zappos

Bruno Marc Men’s Suede Chelsea Boot

If you’re looking for more of a statement shoe, consider this blue suede style from Bruno Marc. Not only will its rich color add subtle flair to any look, but it will also ensure you stay comfortable throughout your day thanks to an included cushy footbed. Available on Amazon, the boot has over 3,600 reviews and boasts an average rating of 4.5 stars. One user noted that the shoe is even “very wide foot-friendly.”

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CREDIT: Courtesy of Amazon

Skechers Men’s Segment-Dorton Boot

Looking for a durable Chelsea boot that’s comfort-driven? Consider the Segment-Dorton Boot from Skechers. The rugged style sits atop an elevated lug sole and features the brand’s signature air-cooled memory foam footbed for hours of support. The buffed leather finish also makes the pair super durable, and adds an edgy look to off-duty outfits. Available on Amazon, the boot comes in four colorways for you to select including dark brown, black, gray and brown.

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CREDIT: Courtesy of Amazon

Ariat Men’s Midtown Rambler Boot

While most Chelsea boots have round toes, Ariat’s Midtown Rambler boot has a trendy square toe. The brand’s take on the classic silhouette offers the perfect combination of a rugged, durable shoe with a bit of a polished Western flair. Wear the boots with sweatpants or joggers for a casual walk outdoors or with jeans and your favorite button-up for a put-together look. Amazon users note that the style runs a bit narrow, but gives off quintessential  “rockstar vibes” for those who are able to find the right fit.

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CREDIT: Courtesy of Amazon

Calvin Klein Men’s Fenwick Chelsea Boot

Calvin Klein’s take on the Chelsea boot is both casual and dressy. The polished leather boot is sleek and effortless thanks to its pull-tab at the back and elastic sidings. The easy-to-wear shoe will effortlessly complement any fall or winter look. Plus, its flexible rubber sole and padded tongue will also help you stay comfortable while you go about your daily routine.

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CREDIT: Courtesy of Macy's

Thursday Boots Co. Duke Men’s Chelsea Boot

Thursday Boots Co.’s Duke boot is stylish and durable thanks to its weather-safe suede upper, which the brand guarantees will only look better with age. The pair also features a full glove leather interior lining and breathable cork bed midsole for comfort. To top it off, this shoe has a Goodyear welt construction, making the boot water-resistant and re-soleable. It also has a studded outsole for extra traction.

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CREDIT: Courtesy of Thursday Boot Co.

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