11 Best Chelsea Boots for Men: Don’t Miss These

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by  William Barton | Last Updated: 

With so many “best of” articles floating around, it’s hard to find one authority who knows what they’re talking about. Anyone can follow hear-say and put a junky boot on their list.

That’s why after wearing dozens of different Chelsea boots and researching for dozens of hours over the past two years, I decided to collect the definitive list of the best Chelsea boots for men.

My Top Pick
  • Italian full grain calfskin leather is buttery smooth
  • Blake stitch construction is recraftable and slim
  • Toe box shape has a sophisticated modern styling
Best for Winter
  • Made with Italian box calf leather, which has a tight grain and beautiful appearance
  • Blake stitch construction is slim, lightweight, and classy
  • The leather sole makes this a dress-Chelsea option
Best Black Chelsea
  • Made with Italian box calf leather, which has a tight grain and beautiful appearance
  • Blake stitch construction is slim, lightweight, and classy
  • The leather sole makes this a dress-Chelsea option
Best Tan
  • Honey Suede option uses water resistant WeatherSafe leather
  • 360-degree Goodyear welt is recraftable and the sole is sturdy
  • Versatile from a style perspective
Best Dress
  • Beautiful box calf leather
  • Modern European toe shape
  • Goodyear welted for greater durability, which is more unusual for a dress boot
Best Budget
  • Trendy light tan with crepe sole Chelsea for an excellent price
  • An excellent alternative to the Common Projects Chelsea
  • Crepe sole gives a lot of shock absorption and comfort
Best YSL Alternative
  • Tall shaped leather heel is higher quality than YSL and less expensive
  • Yearling leather is exquisite and ages nicely
  • It’s crafted from a single piece of leather for a unique shape and greater durability
Best Suede
  • Features suede calf leather, which has a tighter and more refined knap
  • Blake stitch construction is light and flexible
  • Classy leather sole and a variety of suede colors
Best Chunky
  • Goodyear welted construction with wedge sole
  • Extra room in the toe box for greater comfort
  • Made in the USA
Best for Work
  • Steel toe and ASTM rated
  • Waterproof construction
  • Leather pull tab sewn onto the backstay for greater durability
Best Waterproof
  • Made entirely of rubber for 100% waterproofing
  • Polyester lined for comfort—these don’t give you blisters
  • Excellent grip on the soles for walking on wet concrete

I own over 40 pairs of boots, and when I want to dress snazzy, I almost always reach for a pair of Chelsea boots.

They’re slim, stylish, and if the leather is impressive, they make you look like a million bucks. 

I’ve owned Chelsea boots that I love, and I’ve owned a few duds that fell apart, or just looked silly. 

I put together this list of the best Chelsea boots for men because it’s the list I wish I had when I started my journey into the world of boots. I’ve dispensed with the hype (you won’t find Blundstones on here), and I’m only choosing the Chelsea boots I’d buy again.

I’ve broken the list down into different categories so you can find the best version of any specific Chelsea boot style you’re looking for. 

How Did I Come Up with My List?

Time taken to research: Unknown (200 hours?)

Number of products researched: 50+

question icon

It’s impossible to say how much time I’ve spent researching the best Chelsea boots. I’ve been reviewing men’s boots specifically for two years now, and I’ve been professionally reviewing men’s fashion brands for four years.

Throughout that time, I’ve browsed the product pages of probably hundreds of Chelsea boots, I’ve owned different quality leathers, and I’ve learned all about the different construction methods and their strengths and weaknesses. 

I broke this list into different categories (budget, winter, work, etc.) and I carefully selected what I’ve found are the very best Chelsea boots in each category. I own seven of these boots myself. The other four were chosen based on countless hours of research, and what my audience of over 10,000 YouTube subscribers have recommended to me over the years (they know boots). 

There are some notable exclusions, like the Blundstone 550, which doesn’t deserve to be on any “Best Chelsea Boot” list, and I know because I’ve tried those, too.

These Chelseas truly are the best of the best. 

11 Best Men’s Chelsea Boots

My Top Pick: Beckett Simonon Bolton

1.
Beckett Simonon Bolton
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While the multi-month wait time is a bummer, the Beckett Simonon Bolton is the best Chelsea boot on the market. You won’t find a full grain Italian calfskin Chelsea for under $300 elsewhere, and certainly not with this leather thickness.


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Beckett Simonon has an interesting business model you’ve likely never seen before. They hand-make their boots to order. 

On the positive side, the quality is phenomenal for the price.

On the negative side, it can take three months to have your boots shipped to you.

If you need a Chelsea boot in the next few weeks, then I have some other recommendations for you further down in this list, but if you’re looking for the absolutely best value Chelsea boot on the market, the Beckett Simonon Bolton is the winner. 

Made with full grain Italian calfskin leather and a refined Blake stitch construction, the Bolton has all the sophistication and class of a European boot with a modern styling. But it’s not too slim, either (if you want a very slim Chelsea, check out Ace Marks below). 

To me, the Bolton is the perfect balance, and the leather is thick so the boots crease gently over time. That means they’ll stay classy looking even after a year of wear.

What I Like

  • 3mm thick full grain Italian calfskin leather—when you open the box, you immediately understand the level of quality here.

  • The Bolton has a recraftable Blake stitch sole. It’s not great for inclement weather, but it keeps them slim and lightweight, and the Bolton is more sturdy than other Blake stitch boots I own. 

  • The leather options are simple and classic.

  • The price is incredible for the quality you’re getting—I put these on par with my $400 and $500 boots. 

What I Don’t Like

  • It can take up to three months for you to receive your boots. 

What Other Reviewers Say

Beckett Simonon is growing a loyal following, with several reviewers going back for a second or third boot as soon as their first arrives. 

I couldn’t find any complaints about the wait time, though that’s an obvious drawback. But Beckett Simonon does a great job staying in touch with you via email and keeping you updated on your boot’s progress (which isn’t always the case with handmade boot brands that take 3+ months to get to you).

The Verdict

If you can handle the three month wait time, the Beckett Simonon Bolton is the best Chelsea boot on the market. 

You won’t find a full grain Italian calfskin Chelsea for under $300 elsewhere, and certainly not with this leather thickness.

I put my Beckett Simonon boots in the same quality category as my $400 and $500 boots. They’re really that good. 

And from a style perspective, they’re modern and sophisticated without going so narrow that they become uncomfortable.

My Top Pick
Beckett Simonon Bolton
(Get 15% OFF with code Spy15)

While the multi-month wait time is a bummer, the Beckett Simonon Bolton is the best Chelsea boot on the market. You won’t find a full grain Italian calfskin Chelsea for under $300 elsewhere, and certainly not with this leather thickness.


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Best for Winter: Thursday Boots Legend

2.
Thursday Boots Legend

If you’re looking for a Chelsea boot that can stand up to a tough, snowy, rainy winter, then you should check out the Legend.

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Thursday Boots has long been one of my favorite brands, and they’re usually my top recommendation for first time boot-buyers because they’re relatively inexpensive (for high quality boots), and they last a long time.

The Legend is a heavy-lug version of the brand’s original Chelsea boot, the Duke (which is also on this list). Thursday’s StormKing rubber lug outsole has plenty of traction on wet concrete, in snow, and even holds up well on ice. 

Plus, because these boots feature a 360-degree Goodyear welt, you can stand in bad weather for several hours before any dampness starts to work its way into the boot. 

All versions of the Thursday Legend are in Thursday’s Rugged & Resilient leather, which doesn’t need much care at all and is packed with oils and waxes so it’s not going to stain or get soaked easily. 

What I Like

  • The Legend is a low-maintenance boot that doesn’t stain or discolor in the rain and snow. 

  • The StormKing outsole provides a lot of traction on wet surfaces and it doesn’t get clogged with mud.

  • It’s quite slim and stylish for a winter-duty boot.

  • It’s available in sizes 6-16.

What I Don’t Like

  • There are no smooth leather options available—just WeatherSafe suede and Rugged & Resilient.

What Other Reviewers Say

Many reviewers say they enjoy how easy these boots are to slip on and take off, and several reviewers from Minnesota say their feet stayed warm with just the Legend and a thick pair of socks (I guess people from Minnesota like to self-identify). 

The break in is easy, and these are ready to rock right away in the dead of winter.

The Verdict

If you’re looking for a Chelsea boot that can stand up to a tough, snowy, rainy winter, then you should check out the Thursday Boots Legend

The StormKing outsole is fantastic (I’ve been wearing my StormKing Captains all winter long), and the Rugged & Resilient leather is no-fuss and doesn’t pick up salt stains easily. 

The best thing about the Legend is that it’s not a huge, ugly boot. It’s legitimately stylish, and it’s built with enough water resistance and traction that you don’t have to worry about trudging out into the snow.

Best for Winter
Thursday Boots Legend

If you’re looking for a Chelsea boot that can stand up to a tough, snowy, rainy winter, then you should check out the Legend.

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Best Black: Ace Marks Troy

3.
Ace Marks Troy Chelsea Boot

Ultralight full grain Italian calfskin leather gives this boot elegance that's hard to find under $500. Ace Marks keeps things full Italian with a narrow last and Blake stitching for that sleek Euro flair.

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Ace Marks is a relatively unknown brand, but the quality of their Troy Chelsea boot is superb. Made with box calf leather, the creases are very gentle and fine, and this dressier Chelsea pairs well with a suit.

This is the slimmest Chelsea boot on my list (it’s almost the dressiest, but the YSL alternate R.M. Williams takes that honor).

The Ace Marks Troy comes in several different color leathers, but it’s my top black Chelsea boot because black is a more formal color and this is the most formal Chelsea I’ve seen. 

Complete with a leather sole and Blake stitch construction, this isn’t a very tough boot, but it’s extremely stylish and draws a lot of compliments. 

What I Like

  • The Italian box calf leather is super smooth, sophisticated, and it creases gently so these still look fantastic after multiple years (with proper care). 

  • They’re very slim and narrow—combined with a leather sole and the exquisite leather, you get a nice dress Chelsea. 

What I Don’t Like

  • I recommend shoe trees for all your boots, but these especially need them to keep their nice shape. 

What Other Reviewers Say

The style is the biggest reason why most reviewers picked up their Ace Marks Troy Chelsea boots, and that’s the top comment I see in common between most reviews: they’re beautiful.

Many reviewers say these are comfortable, and they are, but comfort isn’t the main feature of this boot. They fit quite snug, and when I wear a thick pair of snugs, it can be a little tight. I recommend either getting your sneaker size, or just sticking with dress socks.

The Verdict

If you want a stunning pair of black Chelsea boots, the Ace Marks Troy is my favorite option. 

The box calf leather has a tight grain that looks beautiful and ages gracefully. This is a fantastic choice for a dress Chelsea if you’re looking to pair your new boots with a suit, too.

Best Black
Ace Marks Troy Chelsea Boot

Ultralight full grain Italian calfskin leather gives this boot elegance that's hard to find under $500. Ace Marks keeps things full Italian with a narrow last and Blake stitching for that sleek Euro flair.

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Best Tan: Thursday Boots Duke

4.
Thursday Duke

The Duke is Thursday’s first Chelsea boot, and it brings the brand's hallmark construction quality and value for money. This is a fantastic everyday Chelsea.

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The Thursday Duke is my go to for an everyday Chelsea. If you’re looking for a tan Chelsea boot, the Honey Suede leather option is your best option (though I also recommend checking out the Sandstone Thursday Cavalier, as that may be more the style you’re looking for). 

But I prefer the Duke over the Cavalier because it’s a little more sturdy and solid while still staying slim and modern looking.

What I Like

  • The WeatherSafe suede is tanned with hydrophobic compounds in its core, so the Duke is weather resistant all the way through—it doesn’t just have a quick spray over the top. 

  • With a Poron insole, cork midsole, and a DuraEVA comfort strip, the Duke is one of the most comfortable boots on this list. 

  • The 360-degree Goodyear welt is recraftable and gives the boot decent water resistance overall so you can wear it every day, even in the rain. 

What I Don’t Like

  • There’s not anything major I dislike about the Duke.

What Other Reviewers Say

Reviewers on Thursday’s website often mention that they’re on their second or third pair of Thursday Boots. Style and quality are the two big words thrown around in a majority of reviews, so if that’s something you’re into (who isn’t?) then check out the Duke.

The Verdict

The Thursday Duke is a versatile tan Chelsea you can rock through spring, fall, and winter. I like to wear Chelsea boots often because they’re easy to slip on and they look good. The Thursday Duke is the boot I reach for most often.

Best Tan
Thursday Duke

The Duke is Thursday’s first Chelsea boot, and it brings the brand's hallmark construction quality and value for money. This is a fantastic everyday Chelsea.

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Best Dress: Carmina Simpson

5.
Carmina Chelsea Boots 80216 Simpson

Made with black box calf leather, the quality of the 80216 is incredible. While it may take some back and forward to find the best last and size for your foot, there's no doubt that Carmina produce the pinnacle of the dress Chelsea boot.

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Carmina is the gold standard for dress Chelseas, so if you know a lot about boots, this shouldn’t be a surprise. 

Carmina has two popular lasts: the Simpson and the Rain. In my opinion, the Simpson is the better of the two choices if you’re looking for a dress Chelsea. 

With a slightly squared toe, a narrow upper, and a low profile instep, the Carmina Simpson Chelsea boot is as dressy and stylish as Chelseas get.

What I Like

  • The box calf leather is supple, tightly grained, and a pleasure to wear. 

  • Unlike many dress boots, the Carmina Simpson Chelsea features a Goodyear welt, so it’s more easily recraftable (meaning you can own it for a decade or more). 

  • Add a metal toe cap at checkout if you want that extra “clack” in your step—it’s a total power move. 

What I Don’t Like

  • Because it’s so narrow, you may want to size up a half size.

What Other Reviewers Say

Some reviewers say that these boots can feel a bit stiff at first, and may fit snug for the first few wears. However, the boot breaks in, the leather loosens up, and they become more comfortable within the first four or five wears.

The Verdict

The Carmina Simpson is what I’m wearing to every wedding I’m going to this year. It looks fantastic paired with a suit. And if you work in a profession that still requires more business-formal attire, this dress Chelsea is a stunner.

It looks rich, it sounds good on hard floors, and after a few wears, the tightly grained box calf leather develops light creases that speak to the quality of the materials and construction.

Best Dress
Carmina Chelsea Boots 80216 Simpson

Made with black box calf leather, the quality of the 80216 is incredible. While it may take some back and forward to find the best last and size for your foot, there's no doubt that Carmina produce the pinnacle of the dress Chelsea boot.

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Best Budget: New Republic Sonoma

6.
New Republic Sonoma

The New Republic Sonoma Suede Chelsea boot is the best Chelsea I’ve found for under $100. 



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The New Republic Sonoma Suede Chelsea boot is the best Chelsea under $100. It’s also a great alternative to the Common Projects Chelsea boot, which I don’t think is worth its high price tag. 

The New Republic Sonoma is a little different than other entries on this list because of its crepe sole. 

This makes it really comfortable to wear, but just watch out: crepe soles can get very dirty very fast. 

Still, the construction and style of this boot is a steal for the price.

What I Like

  • The light sandy suede is an excellent spring and summer style option. 

  • The crepe sole makes for a comfortable wearing experience.

  • The price is low, especially considering the quality.

What I Don’t Like

  • The crepe sole gets dirty quickly and isn’t the most durable. 

What Other Reviewers Say

Many reviewers find New Republic when looking for this light tan style of Chelsea boot—mostly as a cheaper alternative to the Common Projects Chelsea. 

There are a few warnings among the hundreds of crowd-sourced reviews, though. First: get your sneaker size. Those who chose their boot size (which is usually a half-size smaller than sneakers) found their new boots too tight. Get the same size as you would your sneakers.

And second: beware of the crepe sole. It has a unique look and is comfortable, but the sole gets dirty really easily. If you plan on wearing your new boots several times a week, the sole will turn grey in a matter of months. If you want something you can keep clean-looking for a year or longer, choose the Thursday Duke or Cavalier.

The Verdict

The New Republic Sonoma Suede Chelsea boot is the best Chelsea I’ve found for under $100. 

It has its drawbacks—don’t get this boot if you want a dressy look. The main reason is because the crepe sole will get dirty and turn grey. It’s what crepe soles do. Even if you baby your boots, they’ll start to look dirty faster than the other boots on this list. 

But if you’re looking for a casual Chelsea on the cheap, the New Republic Sonoma is my top choice. 

If I scared you away with all the dirt-talk, then check out the sandy suede version of the Thursday Cavalier. It has a leather sole that won’t discolor like the Sonoma.

Best Budget
New Republic Sonoma

The New Republic Sonoma Suede Chelsea boot is the best Chelsea I’ve found for under $100. 



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Best YSL Alternative: R.M. Williams Yearling

7.
R.M.Williams Yearling Boot

Compared to the popular YSL Chelsea, this R.M. Williams Yearling has a much easier to digest price, plus the quality is far better.

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The R.M. Williams Yearling Chelsea is a far better alternative to YSL Chelseas. 

YSL boots have a block heel, which is basically a piece of plastic with a sticker over it. For a $500+ boot, that’s absolutely unacceptable.

For an easier to digest price, with far better materials and construction, I recommend the R.M. Williams Yearling Chelsea. The heel is made with stacked leather and has the same Cuban pointed shape that makes YSL boots stand out. 

If you want the luxury look, R.M. Williams will serve you better than YSL.

What I Like

  • These are wholecut Chelseas with Yearling leather—quality doesn’t get higher than that. 

  • They feature the Cuban-style heel, but with stacked leather instead of a plastic block. 

  • The dual pull tabs in front and back make the boot easier to put on without warping or creasing. 

What I Don’t Like

  • There are only two leather options (though at least one is black). I’d like to see a greater variety of colors.

What Other Reviewers Say

There aren’t many reviews of this boot online, but those that I could find stated they picked these up because they were wary of YSL’s steep price. In every review I found, the owner was pleased with their buy and recommended these boots. 

The Yearling leather especially looks fantastic after a year of wear, though one reviewer was adamant that you get the heel toplift redone as it starts to wear out. He said it’s much easier to replace the heel cap than to replace the entire stacked leather heel (much cheaper, too).

The Verdict

There’s no reason a YSL Chelsea should cost nearly $1,000. They have a block heel—not even the $200 Thursday boots on this list have a cheap block heel. 

If you want true luxury, and want to keep the same Cuban heel style, get the R.M. William Yearling Chelsea boot. It’s about half the price of the YSL Wyatt boot, but has several quality and construction improvements. 

It’s a wholecut, which signifies higher leather quality, and is far more durable while still keeping a similar shape.

Best YSL Alternative
R.M.Williams Yearling Boot

Compared to the popular YSL Chelsea, this R.M. Williams Yearling has a much easier to digest price, plus the quality is far better.

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Best Suede: Velasca Ofele

8.
Velasca Ofele

With suede calfskin leather, the Velasca Ofele is my top pick for a suede Chelsea boot. The knap is finer, the leather is sturdier, and the overall construction and style are well worth the cost.

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There are a lot of amazing suede Chelsea options on this list so far, but if I could only choose one, I’d go with the Velasca Ofele

I like the slimmer elastic goring on the sides of this boot, and the leather sole is classy and elegant. 

There are four different suede options to choose from, and they’re all made with calf-suede, which has a finer knap. 

These suede Chelseas aren’t as easy to care for as some of the Thursday WeatherSafe suede options, so keep these boots limited to days with clear-skies unless you weatherproof them first.

What I Like

  • The four calf-suede options are all richly dyed and look classy. 

  • Details like the brass tacks in the heel aren’t very noticeable, but show Velasca’s dedication to craftsmanship. 

  • These boots are unlined so they’re more comfortable in warmer weather. 

What I Don’t Like

  • The heel is a bit flat—I personally prefer a little more height in the heel. 

What Other Reviewers Say

True to their Italian heritage, these boots are quite slim and stylish, but for some reviewers, they found them a bit difficult to get on at first. 

You should have a shoe horn at the ready when slipping these on for the first time. However, the same reviewers said that the fit was ideal once their foot was in.

The Verdict

With suede calfskin leather, the Velasca Ofele is my top pick for a suede Chelsea boot. The knap is finer, the leather is sturdier, and the overall construction and style are well worth the cost. 

Just be ready to either apply a weatherproofing spray or limit these boots to clear days because the fine suede won’t do well with water.

Best Suede: Velasca Ofele
Velasca Ofele

With suede calfskin leather, the Velasca Ofele is my top pick for a suede Chelsea boot. The knap is finer, the leather is sturdier, and the overall construction and style are well worth the cost.

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Best Chunky: Red Wing Classic Chelsea 

There are some solid contenders for the best chunky Chelsea boot, but to me, the Red Wing Classic Chelsea wins.

You might think Blundstone boots would win this category based on their popularity, but after reviewing both the 500 and 550, I really don’t think Blundstone’s are worth the price. 

The Red Wing Classic Chelsea has a similar upper shape (though I think the second pull tab in the front is really cool and I wish the Red Wing had it). 

The big difference is the wedge sole. You’re either a fan of the style or not. 

Personally, I’m not crazy for the wedge sole, but it offers a lot of slip resistance and it’s super comfortable. Because of that, I use this Chelsea all the time as a chore boot, and I pick up my other Chelseas for more stylish outfits.

What I Like

  • Red Wing’s SB Foot Tanning Company leather is rugged, durable, thick, and ages well without needing much care. 

  • The wedge sole has a lot of traction and is comfortable to stand on all day.

  • This boot features a 360-degree Goodyear welt, which offers a lot more weather resistance and recraftability compared to Blundstones. 

What I Don’t Like

  • I’m not a huge fan of the wedge sole from a style perspective. 

What Other Reviewers Say

Many reviewers say this is the most comfortable Red Wing heritage boot, and I agree. Many reviewers beat their Classic Chelseas up working in them, and while I think there are better work Chelseas available (with steel toes), these are the boots I reach for whenever I’m working around the house.

The Verdict

You either like the wedge sole or you don’t. If you like the wedge sole, then the Red Wing Classic Chelsea is the way to go. I don’t think it’s the most stylish boot, but I find myself wearing these often because they’re so comfortable, offer a ton of weather resistance, and the leather is sturdy enough to take a beating.


Best for Work: Ariat Groundbreaker Chelsea

10.
Ariat Groundbreaker Chelsea

There are few Chelseas on the market that are fit for tough work sites, but the Ariat Groundbreaker Chelsea is ready for the job.

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Ariat makes a huge variety of work boots and they’ve hit the top of many of our best work boot roundups. 

Their Groundbreaker Chelsea is 100% waterproof and features a steel toe, so in addition to being easy to put on and take off, they keep your feet dry and safe. 

I really like that the back pull tab is thick leather and is sewn into the back-stay—if you’re a big burly dude, you’ve likely ripped the nylon pull tabs out of your previous boots, but that’s not going to happen here.

What I Like

  • They’re ASTM rated for work safety.

  • They feature a reinforced steel toe.

  • They’re 100% waterproof, and the leather has been treated with waterproofing as well.

What I Don’t Like

  • There aren’t any composite toe options, so if you work in the cold, the steel toe can get uncomfortable. 

What Other Reviewers Say

Reviewers who rely on the Ariat Groundbreaker Chelsea to keep their feet dry and protected seem happy with their purchase. However, in reading reviews, it looks like many people who use their boots for really tough and rugged work had issues around the 12-month mark.

If you’re in and out of water, working in high temperatures, and facing a lot of impacts every day, expect these to last about a year and not much longer.

The Verdict

There are few Chelseas on the market that are fit for tough work sites, but the Ariat Groundbreaker Chelsea is ready for the job. 

It’s ASTM compliant for work safety and the steel toe is something I wish I had the multiple times I ran a handcart over my feet in the warehouse. 

If you’re working a tough jobsite and wear these everyday, you can expect them to last about a year, but based on reviews, I don’t think they’ll last much longer. For a piece of equipment, however, I think that’s pretty good.

Best for Work
Ariat Groundbreaker Chelsea

There are few Chelseas on the market that are fit for tough work sites, but the Ariat Groundbreaker Chelsea is ready for the job.

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Best Waterproof: Hunter Original Chelsea Boot

11.
Hunter Original Chelsea Boot

Sure, there are waterproof leather boots, but if you want a truly waterproof boot, rubber is the way to go. But don’t just get any rubber Chelsea boot---go with the best. That’s the Hunter Original Chelsea boot. 


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These stylish rain boots exploded in popularity, mainly because they’re one of the few rubber rain Chelseas that are actually comfortable. 

They’re 100% rubber, so you never have to worry about treating the upper, or the sole separating. Unlike many other rubber boots, Hunter’s Chelseas won’t mangle your heel because the rubber is much more pliable than other cheap rain boots. 

And Hunter pulls the look off—I still wouldn’t wear these on a sunny day, but they’re quite slim and stylish so they don’t look like

What I Like

  • Because they’re entirely rubber, they’ll remain waterproof for their lifetime.

  • The tread pattern is specifically designed to keep you upright on wet concrete. 

  • They come in a wide variety of dark, neutral colors. 

What I Don’t Like

  • I’d like to see a version of this boot with a thicker lining and some insulation for the cold and rainy days. 

What Other Reviewers Say

Reviewers on the Hunter site enjoy their rain boots. I did see a few comments mention ordering a half size to full size larger if you plan on wearing thick wool socks with your rain boots, so that’s worth noting.

The Verdict

Sure, there are waterproof leather boots, but if you want a truly waterproof boot, rubber is the way to go.

But don’t just get any rubber Chelsea boot—go with the best. That’s the Hunter Original Chelsea boot

It’s lined and the rubber is pliable so you won’t end up with nasty blisters. Plus, these rubber Chelsea rain boots actually look good so you won’t be tempted to go with your non-waterproof boots instead.

Best Waterproof
Hunter Original Chelsea Boot

Sure, there are waterproof leather boots, but if you want a truly waterproof boot, rubber is the way to go. But don’t just get any rubber Chelsea boot---go with the best. That’s the Hunter Original Chelsea boot. 


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What Are the Different Types of Chelsea Boots?

Not all Chelsea boots are alike. One quick glance at my list will show you that. 

There are five different types of Chelsea boots you should know about before settling on a pair for yourself. I don’t know if these are official categories, but this is how I view the Chelsea landscape.

1. Dress Chelsea

model wearing black ace marks chelsea boots
Ace Marks Troy Chelsea Boot

A dress Chelsea should have three key features: a leather sole, a slim silhouette, and should come in smooth, dark, full grain leather. 

Chelsea boots aren’t typically formal, but if you follow the three guidelines above, you can easily pair these boots with a suit. 

Great examples of a dress Chelsea are the Beckett Simonon Bolton, Ace Marks Troy, Carmina Simpson, and the R.M. Williams Yearling boot. 

2. Everyday Chelsea

Author William Barton modeling Thursday Boots Duke Chelsea boot 1
Thursday Duke

Everyday Chelseas have a little more room in the upper, and should be a tad more comfortable than your standard dress Chelsea. 

For my everyday boot, I want a rubber sole for extra traction and durability, plus thicker leather and greater comfort.

My favorite everyday Chelseas are the Thursday Duke, but some other great options are the Thursday Legend and the Velasca Ofele (though the Velasca Ofele has a leather sole, but the shape is still more roomy, and therefore makes it an everyday type for me). 

Thursday Duke

The Duke is Thursday’s first Chelsea boot, and it brings the brand's hallmark construction quality and value for money. This is a fantastic everyday Chelsea.

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3. Work Chelsea

model wearing Red Wing Classic Chelsea boots
Red Wing Classic Chelsea

These are rugged work boots, and they’re easy to put on and take off. They should have strong traction, thick leather, and be comfortable to stand in all day. 

Work Chelseas are typically more bulbous and not so stylish. One of the most popular versions of this boot are Blundstones. 

While Blundstone may win the popularity contest, I think there are better choices, including the Red Wing Classic Chelsea, Ariat Groundbreaker Chelsea, and the Jim Green Stockman

4. Jodhpur

closeup beckett simonon douglas jodhpur boot
Beckett Simonon Douglas Jodhpur

Jodhpur boots are quite similar to Chelsea boots, and their heritage is closely intertwined, so I’m adding them to this list. Plus, from a style perspective, they’re interchangeable—whenever you want to wear a casual Chelsea, you can also wear a Jodhpur.

Jodhpurs have a similar shape as Chelsea boots, but instead of elastic goring on the sides, they’re closed with a leather strap and buckle. 

My favorite Jodhpur boots are the Beckett Simonon Douglas and the Thursday Rogue

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Beckett Simonon Douglas Jodhpur
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Made with buttery-smooth full grain Italian leather, the Douglas Jodhpur from Beckett Simonon is a substantial and stylish boot.

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5. Wingtip/ Brogue/ Cap Toe

These styles of Chelsea boot are more rare—the wingtip and brogue versions tend to be more dressy. The cap toe Chelsea boots I’ve seen can go either way: sometimes they’re more casual, other times more formal. 

You can find great versions of these boots on the market, but personally, I prefer the simple, understated style of a pure Chelsea. I think lace up boots look better with a wingtip and broguing, and the formality of a lace up boot is better suited to the added ornamentation. 

What’s the Best Color for Men’s Chelsea Boots?

author modeling Thursday Boots Duke Chelsea boots

Depending on how you plan to wear your Chelsea boots, choosing the right color can be a tough call. 

If versatility is what you’re after, then choose a dark brown pair of Chelsea boots, and make it full grain leather—not suede. With dark brown full grain leather, you can wear your boots in casual, smart casual, and business casual outfits, which covers the spectrum of what most people wear on a daily basis. 

Black is the most formal leather option. You can also wear black Chelsea boots with casual outfits. It depends on what the rest of your wardrobe looks like: if you wear a lot of black t-shirts and black jeans, then perhaps black leather is your best choice. 

model wearing grey chinos and black ace marks troy chelsea boots with green shirt

But if you wear a greater variety of colors and tend toward chinos and blue jeans, then I recommend dark brown. 

I picked up my lighter suede Chelsea boots after I’d already owned a dark brown and black pair of Chelseas. While I wear my Thursday Duke Honey Suede boots all the time, they won’t pair well with a suit or a more formal outfit. I picked them up after I had my dark brown and black footwear taken care of.

model wearing mgemi dritto chelsea boot

If you already have dark brown and black pairs of shoes, then you should choose whichever color Chelsea boot you want. 

If not, cover the staples first. Then you can get creative. 

History of the Chelsea Boot

Thursday Boots Cavalier model sitting

Chelsea boots date back to the early 1800’s when they were originally made for Queen Victoria. But it wasn’t until the 1960s that they became a symbol of fashion (they were the boot of choice for The Beatles).

Chelsea boots have a heel and a more pointed toe, but there are many different styles available today.

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The slimmer, more European style of Chelsea boots is the most fashion forward, though some workwear brands have adopted the elastic panel and simple construction for easy on and off wearing. 

There are variations of the Chelsea boot like the Jodhpur boot, which has a buckle and strap rather than the elastic goring, and the Riding boot, which typically has a different heel meant for hooking into stirrups. 

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The popular Yves St Laurent Chelsea boots have a Cuban heel, which is higher than what you normally find on most men’s boots. This style isn’t very common anymore (not many guys are that adventurous with their boots), but some brands like R.M. Williams still offer the fashion forward Cuban heel for some of their models. 

Conclusion

You’re ready to slip on a new pair of boots, right? 

After researching hundreds of brands and trying a dozen or so for myself, I’m confident these are the best Chelsea boots a guy can find.

FAQs

Are Chelsea boots out of style?

No, Chelsea boots aren’t out of style. In the current fashion cycle, guys with a more refined and sophisticated look are wearing Chelseas more, while young guys going for a grungy look are opting for sneakers. If you want to look like you’re in command of your life, a pair of Chelseas will help.

What kind of jeans do you wear with Chelsea boots?

Your jeans should have taper below the knee to match the slim aesthetic of the boot. Avoid straight cut, relaxed cut, and boot cut jeans. Instead, opt for slim or straight taper jeans. Light color jeans match light colored boots, but the most versatile choice for jeans is dark blue.

How formal are Chelsea boots?

Chelsea boots are casual boots, but if you get a dressy version with a leather sole and a fine full grain leather, you can wear them with a suit. For a formal boot, look at Balmoral boots. Chelseas are a step below Balmoral on the formality scale, but can still work as part of a style-forward formal outfit.

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