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Thursday Boots Legend Review: My Experience After a Year

William Barton

Boots, Leather, Heritage Fashion, Denim, Workwear

William founded BootSpy in 2020 with a simple mission: test and review popular men’s boots and give a real, honest opinion. Since then, we've welcomed over 5 million readers on our boot reviews and boot care guides. Reach out to him for your own personalized boot recommendation at william@bootspy.com. Or join 50,000+ subscribers on the BootSpy YouTube channel, or send him a message on the BootSpy Instagram. Read full bio.

Last Updated: Apr 3, 2024
9 min read

I polled my audience of over 50,000 subscribers on YouTube to see which Thursday Chelsea they thought was worth getting. Spoiler: the Legend came in first. But there are some important caveats that I’m going to cover in this review.

I discuss my experience with the Legend, how I think it stacks up against the other Thursday Chelsea boots: the Duke and Cavalier, and whether or not the Legend is worth your hard earned money.

A legend is born
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Thursday Legend
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Bottom line: The Thursday Legend is a solid Chelsea boot, and one of the better Chelsea boots you can get for winter. It’s practically waterproof and the Storm King outsole is durable and offers a lot of grip. The style is unique, but if you like the look, you’ll be pleased with the construction quality.

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  • The balance of rugged and dressy is superb---no other brand does this as well as Thursday
  • They’re practically waterproof with the Rugged and Resilient leather, Goodyear welt, and thick Storm King outsole
  • Lots of sizing variety from 6-16, plus five different color options at the time of writing
  • There are no wide widths available for guys with wide feet

Looking for a weather-ready Chelsea, I turned to one of my favorite brands: Thursday Boots.

Plus, I polled my audience of over 50,000 YouTube subscribers to see which Thursday Chelsea was the most popular and the Legend won.

Here are my thoughts on the Legend after having them for over a year, plus the results of that poll.

The Thursday Legend Came in First in a 1,000+ Person Poll

Thursday Boots Cavalier on model wearing jeans

The BootSpy YouTube channel has over 50,000 subscribers. Recently, I polled my audience to see if they preferred the Duke, Cavalier, or Legend.

I own all three, and I know how I personally rank them.

With over 1,100 votes, the Thursday Legend took the top spot with 495 votes.

The Duke came in second with 341 votes, and the Cavalier was last with only 264 votes.

Thursday Chelsea Boots YouTube Poll Results
The Legend is most popular. The Duke is my personal favorite. But the Cavalier is my go-to for dressy situations.

Thursday Legend Overview

Thursday Legend chelsea boot toe structure

The Thursday Legend is quite similar to other Thursday Boots—in fact, all Thursday Boots are pretty similar in construction and materials. The main difference is always in the shape and style. 

So if you already own a pair of Thursday Boots (you’d be surprised at how many people have two, three, or five pairs of Thursdays), you pretty much can expect the same level of quality. 

The main aspects of the Legend are:

  • It’s a classic Chelsea boot—elastic gores at the side and a sleek shape.
  • Thursday uses their Rugged & Resilient leather, which is a sueded chrome tanned leather—it’s not dressy looking, but it can take a beating and is basically waterproof. 
  • The Legend uses a Goodyear welt construction so it can be recrafted (also helps with water resistance). 
  • It features the Storm King outsole.

I’ll explain those features and what they all mean in more depth later on in the review, but the short story is that the Legend is basically waterproof. It’s not 100% waterproof, so don’t go standing in a river in them. But you can expect dry feet even if you’re caught in a hefty rain storm. 

But beyond being functional, they have the classic slim Thursday style. No other brand I know balances rugged and dressy as well as Thursday. 

Things to Consider Before Buying the Legend

Thursday Legend on model

A lot of people wonder if they should get the Legend or a pair of Blundstones. Let me spare you the thought: get Thursdays. 

If you want a full explainer on why, check out my full Thursday vs Blundstone comparison

However, if you’re feeling like the chunky Storm King outsole is too much for you, then take a look at the Thursday Duke. It’s basically the same exact boot but with a studded rubber sole instead of the lug sole.

If you still want to go slimmer and sleeker, then the Thursday Cavalier is the best choice. 

I compare all three Thursday Boot Company Chelseas in the video below if you’re curious about the differences:

My Hands-On Review

First Impression

Thursday Legend shape demonstration

Quick disclaimer: I own something like 11 pairs of Thursday Boots and I love the brand. So I was already expecting a good experience with these Legends. 

Well, I wasn’t disappointed. 

I picked up the Legend in the Black Matte leather, which sort of reminds me of the Batmobile in The Dark Knight. It’s slick, but not too dressy. 

Thursday Legend style on author william barton

The shape of the Legend is very similar to the Duke Chelsea from Thursday. It’s a bit more rounded, and not quite as angular and narrow as the Cavalier. 

Still, even though there’s a bit of extra room in the toe and instep, these are quite slim and sleek looking. Compared to a lot of other boots, you could consider them more of a “dress boot” style, at least in terms of the shape. 

And that’s what Thursday has always excelled at for me—they have dressier shapes, but pair them with more rugged materials. So you end up with a boot that’s definitely casual, but looks fantastic with a slim pair of jeans.

Leather Quality and Care

Thursday Legend shape and leather aging

The Black Matte leather is a Rugged and Resilient leather, so it has a bit of a sueded texture, though there’s no visible knap to it. 

It’s an oil tanned leather and it naturally has a lot of weather resistance to it, so I don’t worry about getting it wet or trying to weatherproof it with any sprays or anything like that. 

I have the Rugged and Resilient leather on a pair of Captains, Presidents, and Diplomats, and I’ve had those boots fully submerged in rivers, caught in rainstorms, trudged through snow banks—the leather doesn’t really get damaged by water. So if that’s a concern…don’t worry.

Thursday Legend on foot

If you want something dressier, like a smooth leather you can put a bit of shine on, you’ll need to find another style of boot, because the Legend is only available in these Rugged and Resilient leathers (except for the Safari WeatherSafe Suede colorway). 

Caring for Rugged and Resilient leather is a bit different than most leathers and requires some special care, so I created a full guide on how to care for Thursday Rugged and Resilient leather. 

The lining is a thin glove leather, which is soft and helps with comfort and breathability. It runs throughout the entirety of the boot, which is pretty rare in a boot under $200.

Here’s a full video on how to care for the various Thursday leathers.


Thursday Legend sole detail

The Legend uses a 360-degree Goodyear welt construction, though the outsole isn’t stitched, which is a bit of a difference in how Thursday’s Storm King boots are made compared to their other studded sole boots. 

The insole is Poron high density foam, so these boots are immediately comfortable and basically have no break in period at all. Under the insole, there’s cork filler pasted in. When I resoled my Thursday Captains, we examined the cork, and it’s a bit more coarse than what you might find in boots that cost $300 to $400. 

If you’re curious what goes into the Legend, it’s pretty similar to what’s inside the Captain. This video shows my full re-craft of my Thursday Captains after 5 years of wear.

That coarseness means that it can break apart a bit faster and you might feel it through the insole, but I only started to feel that in my Captains a bit after four years of wearing them.

Thursday Legend storm king sole detail

The welt is stitched to a leather midsole, which is starting to show some wear. If that leather ever gets too ragged for you, you can sand it down with a fine grip sandpaper, condition with some Bick 4 or Venetian, and dye the leather black. That’s a bit of an operation, and I don’t think you’d need to do that anytime within the first year or so. 

But if that’s something you’re noticing, it’s actually not that hard of a fix. 

The Storm King outsole is cemented on to the midsole. Ultimately, I’d love to see a stitch that attaches everything together for a little extra security. The biggest possible issue that could happen here is that the sole comes unglued from the midsole. 

Thursday Legend durability demonstration

Usually that doesn’t happen, but I’ve also seen in dozens of comments on my videos, on Reddit, and elsewhere that Thursday’s customer service team is quick to get a replacement out if something like that ever happens. 

I’ve had to go through Thursday’s customer service once and the team was incredible. 

So while I don’t think the lack of a stitch will ever present an issue, if it does, I’m very confident Thursday will fix it quickly. 

Fit and Sizing

Thursday Legend boot shape

Thursday boots are a bit narrow, and they don’t always offer wider sizes (some models have wide sizes—the Legend doesn’t). 

But I have standard width feet and my Thursdays fit perfectly. 

In general, you should size a half step down from your regular sneaker size. This is also typically your Brannock size. So I’m a 10.5D on the Brannock and I get a size 10.5 in sneakers. 

I picked up the Legend in a size 10 and they fit great. 

Here’s a detailed Thursday Boots sizing guide for more information. 

What Do Other Reviewers Say?

The Thursday Boots Legend has a 4.9-star rating with over 1,000 reviews on their site. The two big things that jumped out at me in the reviews is people saying that they ordered their normal sneaker size and the boots were too big, and people trying to condition the Rugged and Resilient leather and messing with the look and texture of the boots. 

So to fix this, order a half size smaller than your sneaker size (what you normally get in shoes). 

As for care: you don’t need to apply any waterproofing spray to these boots. Just leave them alone. If six months down the road you want to condition the leather, you need to do a specific process unique to the Rugged and Resilient line. Here’s my guide to conditioning Thursday Rugged and Resilient leather

Thursday Legend Alternatives

Thursday Duke

model standing wearing Thursday Duke honey suede boots
Rocking my Thursday Dukes

The Thursday Duke is basically the same boot as the Legend, but it has a lower profile studded outsole rather than the lug Storm King outsole. 

If you want a dressier style, but still keep an overall casual vibe, then the Duke is a good choice. Check out some of the chrome tanned smooth leather options. My personal favorite Duke is the Honey Suede. It ages well and looks great with a pair of jeans. 

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.

Check Price Read Our Review

Thursday Cavalier

Thursday Boots Cavalier chelsea boots on model
The pull tab free Thursday Cavaliers

The Cavalier from Thursday is the dressiest of their Chelsea boots. It’s also the least weather resistant because of its leather sole. 

So if you think about ruggedness and dressiness on a continuum, it’d go like this: Legend -> Duke -> Cavalier. 

I have the Cavalier in the Shadow Grey suede, but I actually think the best verison is the smooth black Thursday Chrome leather. That’s the best dress Chelsea under $200 for sure. Plus the last that the Cavalier is built on is a slimmer and sleeker overall. 

Thursday Cavalier

The Thursday Cavalier is Goodyear welted, leather lined, and offers excellent value. This particular Shadow Grey version is forever battling it out for the title of my favorite casual everyday Chelsea boot, and even with 20+ pairs of shoes in my closet, it's very often my go-to.

Check Price Read Our Review

My Thoughts Overall

What I Like

  • The balance of rugged and dressy is superb—no other brand does this as well as Thursday.

  • The Legend is practically waterproof with the Rugged and Resilient leather, Goodyear welt, and thick Storm King outsole.

  • Lots of sizing variety from 6-16, plus five different color options at the time of writing.

What I Don’t Like

  • It’d be nice to see wider widths (EE or higher) available for the Legend. 

Who is the Legend for?

The Thursday Legend is the perfect boot for you if you’re looking for a weather resistant Chelsea you can slip on and walk into a rain storm. If you want a rugged Chelsea that doesn’t look like a bulbous clown shoe, you’d be surprised at how hard that is to find—the Legend is a great choice and the price is excellent.

The Verdict

The Thursday Legend is one of the only weather-ready Chelsea boots that’s not huge and round. It actually still almost looks like a dress boot. 

However, with the Rugged and Resilient leather and heavy lug Storm King outsole, you get a definitively rugged and casual look, but not so much bulk that it looks like you’re wearing clown shoes. 

The quality of materials and construction is excellent considering the price of the Legend. Plus, I love that you really don’t need to do much to care for the leather at all. 

Some guys might need a wide size, so that’s a bit of a letdown for dudes with E or EE width feet. 

But if you’ve got standard width feet, then you’ll have no trouble finding your size. 

All-in-all, the Thursday Legend is the Chelsea boot I like to walk into the rain with. It beat my Blundstones by a mile and they look great even when the weather is clear outside.

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.

Check Price


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