The Edit / Our Top 5 Men's Chelsea Boots for Fall 2022


The Best Men's Chelsea Boots for 2022 Are Amazingly Comfortable, Stylish & Affordable

Reviewed by Matt Hayes, Co-founder / Men's Editor

Last Updated October 2022

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Fall is finally here and with boot season upon us once again, we set out to find the best chelsea boots for guys that money can buy.

We looked for that hard-to-find winning combination of: 1) most comfortable; 2) sharpest-looking and 3) the best value-for-money. 

And the winner surprised us. This upstart brand is relatively new on the men's fashion scene, but with their attention-to-detail, style, craftmanship and outstanding value, it's safe to say these won't be the last pair we buy.

Without further ado, these are our pick for the top men’s chelsea boots for fall/winter 2022 👇

The Best Men's Chelsea Boots for 2022: The Chelsea Boot by Amberjack

For the ultimate combination of looks, comfort and value, we think Amberjack’s Chelsea boot is going to be the best bet for most people.

The Chelsea comes in a wide variety of colors and has options for both full-grain leather and suede. Amberjack is a relatively new upstart in the men’s shoe market, but are quickly making a name for themselves with beautiful, luxury-feeling boots for men at a fraction of the price. Amberjack’s Chelseas were the most comfortable we’ve tested, with heat-activated insoles and a plush buck skin lining making them comfy enough to wear for hours on end. Our chestnut leather pair looked fantastic with a pair of dark denim jeans. At $195, they feel like a bargain; and with a 4.9 star rating out of five, it’s clear almost everyone agrees with us.

Why we're loving our Amberjack boots:

  • Cushiony, heat-activated foam insoles are super comfy
  • Offer 8 beautiful colorways, with both leather & suede options
  • Rated 4.9 out of 5 stars 
  • Featured as a top men's dress shoe pick in GQ, Rolling Stone & Forbes

If you’re looking to step up your fall wardrobe and you don’t want to break the bank, we think Amberjack’s Chelsea boot should be your #1 pick.

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The Chelsea Boot

$195 or as low as $18 / mo.

Designed in Brooklyn, NY and produced in one of Portugal's top tanneries, Amberjack's Chelsea boots are an amazing value for money, with comfort, style and versatility that rivals boots that cost 2-3x more.


Ratings Breakdown


The leather is full-grain, hand-crafted and feels premium all-around. And the comfort is simply unmatched relatively to any boot we've tried 


You’re paying a fraction of what you’d pay with vs. high-end department store brands


The website is beautiful and easy-to-use and the packaging and unboxing experience is exactly what you'd expect from a modern brand


Amberjack is a relatively new brand so you likely haven't heard of them (yet), but don't let that deter you from giving them a try


Free shipping, easy, risk-free returns, plus 0% APR financing options and fast, convenient shipping -- everything you want when buying online

Shop our #1 Pick:

The Chelsea Boot by Amberjack

Other Options Worth Considering:

The Winter Chelsea Boot by Common Projects

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 If you're looking to see and be seen, these are the Chelsea boots to do it in. These sleek and sexy Italian leather boots from fashion house Common Projects are sure to turn heads. 

$672 at Sak's Fifth Avenue
Currently sold out

The Chelsea Boot by Morjas

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These beautiful Spanish-made all-leather Chelsea boots boasts a striking, timeless silhouette similar to the Common Projects boots, albeit at a more palatable pricepoint. 

$395 at Morjas

Rothy's Chelsea Boot in Merino Wool

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If you’re a bit more adventurous, check out their Granite Black pair, which boasts a merino wool blend fabric paired with an urban camo-patterned counter panel for a bit more edge.

$259 at Rothy's