10 Best Chelsea Boots for Men

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From Kanye West to The Beatles, Chelsea boots have been an iconic footwear choice for men for several decades.  Not only are these the boots of trendsetters, but they are also an effortless way to demonstrate your unique personality.

Below is a list of the best Chelsea boots for men of 2021.  These boots showcase quality craftsmanship, uncompromising attention to detail, and perhaps most important, provide you with a comfortable step wherever your next adventure takes you.

Comparing the Best Chelsea Boots for Men

Rhodes Footwear Huxley BootBest Overall
Suede Chelsea Boots – Brooks BrothersBest Suede
Nisolo Javier Chelsea BootEthically Made
Red Wing Heritage Weekender Chelsea BootMade In USA
Bitflex Chelsea – AstorflexTimeless Style
Brook Brothers Chelsea BootsFormal
Bruno Marc Men’s Suede Leather Chelsea Ankle BootsAffordable (Under $100)
Aquatalia Adrian Leather Chelsea BootsLuxury
Jude Boot In Tonal by  TaftUp & Coming
Thursday Boot Company Duke Men’s Chelsea BootBest Value

Best Chelsea Boot Overall

Rhodes Footwear Huxley Boot

When it comes to quality Chelsea boot brands, Rhodes Footwear is among the best.  Striking that perfect balance between both fashion and function – the Huxley Boot is a classic Chelsea boot that will quickly become a wardrobe favorite for many.  Relying on a premium calf leather upper, it will be both intensely durable and breathable.  What truly sets this boot apart from many others is the anti-shock insole from Texon.  Some men claim that it feels like you are “walking on clouds.”

One nice feature that men like about this boot is the welt.  Relying on Blake stitching, the outsole is easy to replace.  Therefore, if the leather upper remains in good shape, you can bring these to your local cobbler to have them repaired once the outsole begins to wear down.

Key Features

  • Leather Type: Calf Leather
  • Welt: Blake
  • Closure: Elastic Band
  • Sizes Available: 8-13
  • Country of Origin: Portugal

Best Suede Chelsea Boots

Suede Chelsea Boots – Brooks Brothers

Anyone looking for a classy boot to add to their closet should virtually make their way on over to Brooks Brothers and grab a pair of Suede Chelsea boots.

These guys rarely miss a beat when it comes to crafting quality shoes. Made from buttery brown suede and leather soles, they look and feel great.

Complete with tonal stitching and a perfectly rounded toe, these are the ultimate statement boots! Whether you’re roaming through city streets or heading on a fall vacation with your sweetheart—these top-rated Chelsea boots will not disappoint.

Key Features

  • Leather Type: Suede
  • Welt: Not Disclosed
  • Closure: Elastic Band
  • Sizes Available: 8-13
  • Country of Origin: Italy

Ethically Made

Nisolo Javier Chelsea Boot

The perfect fall boot has arrived.  Whether you are walking through a pile of wet leaves or down a wet street with several puddles around, you will love that the Nisolo Javier Chelsea Boot is naturally water-resistant.  Paired with a 1.25″ rubber heel cap, it will also provide confidence with each step as it shouldn’t slip easily.  With an elastic side closure along with a leather pull-tab, these boots should be easy to slide on before you head out the door.  Nisolo makes this boot in three colors: black, brandy, and brown.

Nisolo, as a company, prides itself on its ethical operations (learn more).  If there was ever a time to vote with your wallet, it’s now.

Key Features

  • Leather Type: Top, Full, or Nubuck (source)
  • Welt: Goodyear (source)
  • Closure: Elastic Band
  • Sizes Available: 8-13
  • Country of Origin: Peru

Made in the USA

Red Wing Heritage Weekender Chelsea Boot

Known for their premium leather goods, Red Wing Heritage sets the bar that all other heritage companies must follow.  While most Chelsea boots are made for more sophisticated or formal wear, Red Wing Heritage decided to go against the grain and offer up an ultra-comfortable yet still stylish, weekender Chelsea boot.

Still relying on that classic full-grain nubuck leather that we have grown to love in many products from Red Wing Heritage, you can expect the leather uppers on this boot to last you for years.  When cared for properly, the leather will also develop a lovely patina with time.

Underneath the shoe, you have a textured outsole that provides an excellent grip in slippery conditions.  Relying on stitch-down construction, the outsoles are repairable when worn down – greatly extending the boot’s life. 

Plus, they are made in the USA – what’s not to love?

Key Features

  • Leather Type: Full Grain, Nubuck
  • Welt: Stitchdown
  • Closure: Elastic Band
  • Sizes Available: 7-13
  • Country of Origin: USA

Most Stylish Chelsea Boots

Bitflex Chelsea – Astorflex

The Bitflex Chelsea boot is everything you’ve been looking for and so much more.

Handcrafted by master shoemakers in Northern Italy, Astorflex has been making shoes for over six generations. I think it’s safe to say that these guys know what they’re doing.

These boots rely on premium European leather aged to perfection for 30 days. They are then softened into supple nubuck and mounted on a 100% natural rubber sole for the perfect balance of style and comfort. The Bitflex is also available in nine different colors.

Key Features

  • Leather Type: Nubuck Leather
  • Welt: Blake
  • Closure: Elastic Band
  • Sizes Available: 7-15
  • Country of Origin: Italy

Best Formal Chelsea Boots

Brook Brothers Chelsea Boots

Made in Italy, these tonal stitched Chelsea boots by Brook Brothers offer a classic yet elegant style.  With their slightly moderate ankle height, they won’t rub awkwardly on your leg while still providing adequate support.  They will be a versatile boot to add to your wardrobe.

Sizes vary; however, you can only get these boots in either brown or black.  Crafted from full-grain leather, they should last you for years while also developing a nice patina.

Some men note that these boots run a bit smaller, so you may want to size up just a half-size to account for this. Lastly, these Chelsea boots are available in both black and brown.

Key Features

  • Leather Type: Full-Grain
  • Welt: Not Disclosed
  • Closure: Elastic Band
  • Sizes Available: 8-13
  • Country of Origin: Italy

Best Affordable Chelsea Boots (Under $100)

Bruno Marc Men’s Suede Leather Chelsea Ankle Boots

The Bruno Marc Men’s Chelsea Boots are the perfect pick for those men on a tight budget.  Ringing up at a fraction of the price of other Chelsea boots reviewed, the Bruno Marc’s features a suede upper and a fairly comfortable insole.

While absent of trademark qualities, including a Blake or Goodyear welt, these boots should be able to last you a season or two before replacement.

The boots are easy to slide on and off thanks to the elastic band closure.  Bruno Marc makes this boot available in nine different colors – so you should have no problem finding the perfect boot for you.

Key Features

  • Leather Type: Suede
  • Welt: Not Disclosed
  • Closure: Elastic Band
  • Sizes Available: 7-15
  • Country of Origin: Likely China

Best Luxury Chelsea Boot

Aquatalia Adrian Leather Chelsea Boots

The masterful Italian shoemakers at Aquatalia have bestowed upon us a one-of-a-kind Chelsea boot. These polished leather boots embody the ultimate in rugged sophistication.

These shoes are constructed with a luxurious deep brown leather upper and set on a sturdy heel and well-crafted sole. Details like the water and stain-resistant finish and elastic goring for quick on-and-off make these perfect for men on the go.

Pair with a slim cut trouser and your favorite button-down, and you’ve got a versatile look that can transition effortlessly from day to evening.

Key Features

  • Leather Type: Calf Leather
  • Welt: Likely Goodyear
  • Closure: Elastic Band
  • Sizes Available: 7-13
  • Country of Origin: Italy

Up & Coming

Jude Boot In Tonal by Taft

The Jude Boot In Tonal by Taft is a durable and comfortable Chelsea boot that quickly becomes a favorite brand among men.  Relying on Spanish Suede and a full-grain leather outsole with rubber inserts, this boot will equally feel and look great.

Cobblers can resole the Jude Boot thanks to the reliance on a Blake stitch.  Therefore, you can expect these boots to last you several years. The Jude Boot has an elastic band closure which makes it easy to slide on and off.

Lastly, the color and size varieties are a strong point for this boot.  With three different colors and available in sizes 6 to 15, you should have no problem finding the perfect boot for your unique style.

Key Features

  • Leather Type: Spanish Suede
  • Welt: Blake
  • Closure: Elastic Band
  • Sizes Available: 6-15
  • Country of Origin: Spain

Best Value Chelsea Boot

Thursday Boot Company Duke Men’s Chelsea Boot

Founded in 2014, NYC-based Thursday Boot Company strives to offer ridiculously high-quality footwear at an honest price.  And with the Duke Men’s Chelsea Boot, they appear to be hitting all the right notes.

For starters, this boot relies on a Goodyear welt – making for much better construction while also able to be repaired quickly.  Thursday Boot Company makes the Duke Men’s Chelsea Boots in five distinct uppers.  For their signature Honey Suede, they rely on WeatherSafe Suede that has a blended solution to keep your feet dry while also protecting the suede (source).  Other boots from the same line rely on chrome leather.

These boots’ unique features include the DuraEVA™ comfort strip, cork midsoles, and microbial insoles to give your feet a comfortable and odor-free ride. 

Key Features

  • Leather Type: Varies (Suede, Veg Tanned Leather)
  • Welt: Goodyear
  • Closure: Elastic Band
  • Sizes Available: 6-15
  • Country of Origin: Likely Mexico

7 Considerations When Buying Chelsea Boots

When buying Chelsea boots, keep the following considerations in mind:

1. Material

Chelsea boots rely on any of the following materials; here are their key differences:

  • Top Grain: The top exterior of the cowhide is used for this type of leather.  It is then sanded and buffed to remove surface imperfections.  With time, it develops a nice patina.  Top-grain is premium-grade leather.  Nubuck leather is a type of top-grain leather.
  • Full Grain: This leather is made from the entire cross-section of the hide.  It’s thicker and more durable.  The break-in period of this leather type is longer, and the boot may feel stiffer.  Like top-grain, it develops a nice patina.  
  • Genuine Leather: This leather relies on various parts of the hide – which are bound together by glue.  This leather is susceptible to stretching and tearing.  It’s affordable and suitable for a Chelsea boot intended to be worn for only one or two seasons.
  • Calf Leather or Calfskin:  Sourced from young cattle, it has a delicate and velvet-like texture.  Calfskin is often used by premium brands, given the quality.  It will also develop a nice patina.
  • Suede: This leather, sourced from the underside of the hide, isn’t as durable.  Suede requires special cleaning.  You can expect suede only to last you a few years.

2. Color

Unless worn for a specific look, you will find that most Chelsea boots come in neutral colors  (i.e., tan, black, grey, stone, etc.).  Neutral colors are more versatile, allowing them to work with a wide range of your wardrobe.  Consider darker Chelsea boots if you attend semi-formal events frequently.

3. Ankle Closure

Chelsea boots come with two main side closures:

  • Slip-On / Elastic: The most popular side closure. Allows for a better range of motion when it comes to walking and ankle mobility while keeping the boot secured to your feet.  This closure is also most traditional and versatile.
  • Zippered: While you will see zippers on higher or mid-calf boots, when it comes to Chelsea boots, they are not all that common.  However, the zipper can make the boot feel more secure.  Dirt and debris may cause the zipper to jam, so clean accordingly.

4. Heel Height

Most Chelsea boots have a relatively short heel that is akin to a work boot.  At only a fraction of an inch, the heel won’t be too noticeable when walking.

However, some Chelsea boots do have what is called a Cuban heel.  Cuban heel Chelsea boots are raised about 1.5″ and can give you a much taller appearance. The Cuban heel is often found on cowboy boots (source) and has a slightly tapered cut.

Here’s how both of these heels compare:

Consider a Cuban heel Chelsea boot if you want to add some height.

5. Welt / Repair

To get better value out of your purchase, buy a pair of Chelsea boots that contain a Goodyear welt or Blake stitch.  These welts can be replaced and repaired by your local cobbler.  The welt is crucial if you decide on a pair of full-grain leather boots that are intended to last you for several years.

Cemented and stick-on soles are glued together, making them unrepairable.  If the company doesn’t disclose the type of stitching, assume they’re cemented.

6. Sizing

Sizing varies from one brand to the next.  Often, Chelsea boots run a half-size larger – so size down accordingly.  Always read the product fit details provided by the company carefully.   

It’s essential to get accurate sizing as Chelsea boots don’t have laces.

7. Price

The price largely varies based on the materials, welt construction, and the brand’s reputation.  Expect to pay the following:

  • Inexpensive (Under $100): Often made from genuine leather and non-resoleable.  Generic or budget-focused brands.
  • Average (Between $100 to $200): Some premium leather grades.  It may or may not be resoleable.  Reputable brands.
  • Luxury (Over $200): Premium leather grades.  Resoleable.  Designer and heritage brands.
About Shawn Burns

Shawn Burns is the founder and senior editor of Tools of Men. He started this site with the goal of teaching men proper grooming habits and sensible style. Shawn's expertise includes in-depth product reviews and how-to articles. Shawn was recently featured in the Wall Street Journal for his expertise.

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