The 7 best men’s Chelsea boots that go with everything in your closet — starting at just $39

·4 min read

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Many consider Chelsea boots to be one of the signature footwear styles of the fall and winter seasons, but, in reality, they’re the perfect year-round style. Think about it — they’re incredibly versatile and come in a variety of styles, materials and colors. 

If you’re on the market for the perfect men’s Chelsea boot but you’re overwhelmed by the wide variety of options available across the Internet, we’ve made shopping a bit easier. Below, we’ve listed the seven best men’s Chelsea boots you can buy, separated into categories.

Shop everything from the best overall pick (that’s also machine-washable and crafted from sustainable materials) to the most affordable option that starts as low as $39.09 on Amazon.

Take a look at each style in a bit more detail below.

1. Best Overall: Rothy’s Merino Chelsea Boot, $275

Credit: Rothy’s
Credit: Rothy’s

Buy Now on Rothy’s

Let’s be honest — sustainable fashion can sometimes look a bit questionable. Rothy’s is one of the few brands that executes this ethically conscious theme while remaining on-trend and fashionably sound.

The brand’s recently released Merino Chelsea Boot comes in three classic colors (dark chocolate, granite black and bourbon) and features a blend of premium Merino wool and Rothy’s’ signature thread spun from plastic bottles. While they offer the classic, clean Chelsea boot silhouette, they’re extremely comfortable and perfectly mold to the shape of your foot without squeezing or straining your toes.

2. Coziest Pair: UGG Neumel Chelsea Boot, $130

Credit: Urban Outfitters
Credit: Urban Outfitters

Buy Now at Urban Outfitters

Now, if you’re looking for a pair that’s perfect for rocking exclusively during the colder months, these UGG Neumel Chelsea Boots are the ones to buy. The gorgeous chestnut brown color is the ideal autumn shade and, in true UGG fashion, these suede boots are super plush thanks to their soft wool lining.

These will keep your feet warm and in style all fall and winter long.

3. Most Affordable: Bruno Marc Men’s Suede Leather Chelsea Ankle Boots, $39.09 – $42.49

Credit: <a href="https://www.intheknow.com/tag/amazon/?utm_source=internallinks&utm_medium=internallinkstransactions&utm_campaign=internallinksamazon" data-ylk="slk:Amazon" class="link rapid-noclick-resp">Amazon</a>
Credit: Amazon

Buy Now on Amazon

It’s true — Chelsea boots can be a little expensive, but they don’t have to be. These No. 1 best-selling Bruno Marc suede Chelsea ankle boots have over 5,000 five-star reviews on Amazon and start at just $39.09!

Ranging from sizes 6.5 to 15, these simple Chelsea boots are made of quality materials and come in nine colors, including classic black, camel, tan, grey and navy.

4. Best Classic Choice: Cole Haan GrandOS 360 York Chelsea Boot, $119.97 (Orig. $250)

Credit: <a href="https://www.intheknow.com/tag/nordstrom/?utm_source=internallinks&utm_medium=internallinkstransactions&utm_campaign=internallinksnordtrom" data-ylk="slk:Nordstrom" class="link rapid-noclick-resp">Nordstrom</a> Rack
Credit: Nordstrom Rack

Buy Now at Nordstrom Rack

Cole Haan is one of those premium shoe brands that everyone knows and loves, so it’s no secret that the brand’s Chelsea boots are clear best sellers.

Its GrandOS 360 York Chelsea Boot is water-resistant and features an ultra lightweight foam midsole to give you all-day comfort. Also, these boots boast a classic silhouette that easily upgrades any look, so get them while they’re still in stock.

5. Edgiest Boot: Dr. Martens Wincox Smooth Leather Buckle Boots, $160

Credit: Dr. Martens
Credit: Dr. Martens

Buy Now at Nordstrom

Buy Now at Dr. Martens

Buy Now at Urban Outfitters

For those who prefer an edgier look, these Dr. Marten Chelsea boots definitely fit the bill. The Wincox is a moto remix of the standard Chelsea boot, giving the classic style a vintage biker flair complete with a buckled harness and gunmetal hardware.

Pair these funky boots with anything from black skinny or slim jeans or slacks, and you’re sure to get stares for all the best reasons.

6. Best Waterproof Option: Sorel Cheyanne II Waterproof Chelsea Boot, $89.97 (Orig. $145)

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Credit: Nordstrom Rack

Buy Now at Nordstrom Rack

Rain or snow shouldn’t stop you from rocking some stylish Chelsea boots. In fact, they should encourage it. These best-selling Sorel Cheyenne II Chelsea boots feature a completely waterproof duck toe for maximum functionality. They also feature dual side gore panels, vulcanized rubber shell toes and waterproof leather construction, making them perfect for battling the elements.

Choose between elk black and black dark grey when shopping for the perfect waterproof Chelsea boot moment.

7. Top Chunky Sole Pick: UO Baldwin Leather Boot, $99

Credit: Urban Outfitters
Credit: Urban Outfitters

Buy Now at Urban Outfitters

Chunky boots are having a moment right now, and these Baldwin leather Chelsea boots from Urban Outfitters embody this trend perfectly.

Available in three colors (black, dark brown and off-white), these boots give the classic silhouette a modern upgrade with a bold, stacked rubber sole with grippy traction. They also feature elasticized paneling and pull tab accents for an easy on/off. Trust me — these will quickly become your new favorite fall and winter boots after just one wear. 

If you enjoyed this story, check out this $22 men’s fleece robe that’s peak at-home comfort goals.

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