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

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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.

  • Best Overall: Rothy’s Merino Chelsea Boot

  • Coziest Pair: UGG Neumel Chelsea Boot

  • Most Affordable: Bruno Marc Suede Leather Chelsea Ankle Boots

  • Best Classic Choice: Cole Haan GrandOS 360 York Chelsea Boot

  • Edgiest Boot: Dr. Martens Wincox Smooth Leather Buckle Boots

  • Best Waterproof Option: Sorel Cheyanne II Waterproof Chelsea Boot

  • Top Chunky Sole Pick: UO Baldwin Leather Boot

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

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

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

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)

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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