[Updated December 2023]

The Chelsea boot has got to be one of the most versatile pieces of footwear a man can own. Depending on the parts that go into it, you can find a pair that will go with a suit to the construction site. Even better? Any of them can be thrown on in a few seconds as you head out the door.

This versatility has meant this type of boot has seen an explosion in popularity over the past ten years. Overall, this is a great thing – more options are always better for the customer. However, it also creates a problem: what’s the best Chelsea boot for your budget? Here we are going to take a look at boots ranging from under $200 to well over $1,000 to help you find out.

Before we begin though, let’s talk about what a Chelsea boot actually is. Originally invented so that Queen Victoria could slip on a riding boot quickly, it’s been a boot worn by everyone from the Beatles to Australian cowboys. The defining feature is elastic panels along the side of the ankle – and the total lack of laces.

This simplicity means that shoemakers really need to bring their A game. You can’t hide flaws in the leather, or issues in the stitching. Any imperfection will be clearly visible to any buyer.

One more thing before diving in. This boot will focus on boots that err slightly on the more formal side. There are some great work-boot Chelseas out there, but this was a reader-requested post and their ask was less work-boot.

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What’s the best Chelsea Boot for under $200?

Winner: Thursday Boot Cavalier $190

While I don’t quite agree with a lot of other boot reviewers who view Thursday in the same realm as some of the more expensive brands, if you only have two Benjamin’s in your pocket, there is no better option out there. In fact, I wouldn’t recommend anything else at this price point.

Even more amazingly, they’ve been able to keep this price point for nearly a decade, even after the current inflation.

The Thursday Cavalier is a good-looking boot that can last you for as long as you need it to and comes in a bunch of different colors and leathers. If this is the boot you choose, you likely won’t be disappointed for the money that you’ve spent.

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What’s the best Chelsea Boot for under $300?

Winner: Helm Finn $265

Runner Up: Meermin Chelsea $240

Moving up a few dollars from the last section, there are two great choices for a Chelsea boot priced less than $300.

For my money, I would recommend the Helm Finn (full review here). Since reviewing these, they have been one of my go-to pairs of boots. Sitting by my door, they are built up enough that I don’t mind throwing them on if it’s a bit rainy or muddy, but polished enough that I can wear them to work too.

Helm is also just an easy company to work with for this price level. They offer free shipping and returns, a huge amount of sizing options, and even have a program to sell used boots back to them.

All that being said, the Finn is by far the least dressy boot on this list. If you are in this price bracket and want something a bit closer to a boot for the office, I would suggest taking a look at the Meermin Chelsea.

The boot offers great value – nice materials, an elegant last, etc. Where Meermin hiccups is the purchase itself. Hard to fit lasts combined with expensive shipping and returns means getting into the world of Meermin takes some time and money.

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What’s the best Chelsea Boot for under $400?

Winner: Grant Stone Chelsea $360

Runner Up: Bordon Isidro Chelsea $349

It probably won’t be a surprise to anyone who has read this site before, but if you want to spend around $400 on a Chelsea boot, I think that Grant Stone is the obvious choice.

The Grant Stone Chelsea is made with the same attention to detail as all their boots. That is to say, nearly perfect. Add in top-notch materials, and this is a tough pair to beat. My only real complaint is the last, which does not work for a lot of people (including myself). Of course, everyone will fit lasts differently and you might find this to be the best fit for you.

Another option in this price point is the Bordon Isidro. Like the Helm Finn above these are a bit bulkier than others, but they earned their place based on the materials. These $350 boots, which by all accounts are well made, use Wicket and Craig’s amazing Latigo leather.

To put that in perspective, going from Chromexcel to W&C Latigo on a pair of Nicks is a $200 upgrade.

Of course, you shouldn’t buy a pair of boots based solely on the upper leather, but the Bordons manage to attach a well-made product around that hide as well. Definitely an option to consider if you’re a leather enthusiast.

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What’s the best Chelsea Boot for under $500

Winner: Oak Street Bootmakers 5504 $498

A few years ago, this was one of the most packed price points for this type of boots. However, due to recent inflation, there are just not that many choices here.

Thankfully, you have a great option available in the Oak Street Bootmakers 5504. Why is it named after the 5504 last when all their other boots have a traditional name? I have no idea!

The big benefit to going with the Oak Street Bootmakers Chelsea is that you’re now getting a boot made entirely with materials and labor from countries with strict labor standards. While that might not matter to some, it does to others and it is undeniable that there are costs associated with using these materials and factories.

Of course, the quality is great as well. While Oak Street Bootmakers have had some hiccups in the past, in recent years they have really nailed down their manufacturing. You won’t regret picking this pair up if you value made-in-America boots.

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What’s the best Chelsea Boot for under $600

Winner: R.M. Williams Craftsman $539 or R.M. Williams Comfort Craftsman $539

This is it – the Chelsea boot to buy if you want to buy the classic. This is a Brooks Brothers Oxford Cloth shirt. The Kleenex brand tissue. You get it.

There is no brand more closely linked to this boot shape than R.M. Williams. There are probably plenty of people out there who didn’t even know the brand made anything other than Chelseas.

To be clear, these boots are not perfect. There are little things like the unfinished edge of the back lining that can get caught. Their owners have somehow tried to make the brand even less approachable than it was when they were owned by LVMH. Etc.

However, the design is as classic as can be, they will be plenty durable, and they will go with everything from a suit to denim and a flannel. Give me an unlimited budget for a Chelsea, and this is the one I would pick. In fact, I have.

There are others in this price point, but you shouldn’t buy them. Get this instead.

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What’s the best Chelsea Boot for under $1000

Winner: John Lofgren LK-027 $900

Runner Up: Viberg Chelsea $840

Moving up a tier from the R.M. Williams, you start to get into the smaller batch manufacturers.

The obvious choice here is the John Lofgren LK-207. Made in Japan, these boots really focus on the small details. Things like using soft Japanese cowhide as a liner, or subtle curves in the welt. These start to qualify as artwork as much as footwear.

Unfortunately, these are going to be out of reach for a lot of people, even if you can afford them. Their sizing only goes up to 11, so many people won’t be able to buy a pair that fits. Even if you can, they are made in very small batches so snagging a pair can be difficult. However, if the stars align for you, they are great boots.

Alternatively, Viberg also offers a well-made Chelsea for those who want something a bit more durable than the R.M. Williams offerings. It’s true that Viberg won’t have the same attention to detail as the John Loftgren (or even the R.M. Williams) they do offer a boot that can stand up to a day of physical labor all while looking entirely acceptable in an office environment. Not an easy task.

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What’s the best Chelsea Boot for Any Price?

Winner: Edward Green Newmarket $1,750

Not to be confused with their oxford named the “Chelsea,” the Newmarket Chelsea Boot is simply the best off-the-rack Chelsea available for most guys. Using the best materials with the finest craftsmanship, I doubt anyone will be disappointed with what comes out of the box.

The Newmarket isn’t cheap, but it is the end game Chelsea. At least, the endgame until you go into personally made.

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Wrap Up

There you have it, 10 Chelseas ranging from $200 to $2000 dollars. Think there is one I missed? That something suggested here doesn’t belong? Comment down below if you have any advice for the Chelsea buyer out there.