1-Year Thursday Legend Review: Why is it Thursday’s Best Selling Chelsea?

After about a year of off-and-on wear and after seven years of testing boots, I’m finally trying out the most popular Chelsea from the most popular boot brand, Thursday Boot Company.

I’ve reviewed over a hundred boots on YouTube, visited boot factories all over the world, and even handmade my own boots in Guatemala with leather I made in Mexico — so I have a decent idea of how to judge a boot!

Below I’m going to tell you why I think the Legend has crept to the top of Thursday’s bestsellers, I’ll compare it to the brand’s other Chelseas and those of their leading competitors, I’ll break down sizing, and I’ll tell you their downsides. You’re a busy guy, so let’s start at the end: a summary list of pros and cons!

Pros & Cons Thursday Legend Boots

If you’ve got things to do, here’s my short takeaway.

What I like about Thursday’s Legend

• Excellent value
• Resoleable and practically waterproof
• Rare balance of sleek and casual
• Grippy sole; more “all terrain” than most Chelseas
• Low maintenance leather
• Good comfort, no break in, great shock absorption
• Good range of sizes and widths

Downsides but not deal breakers

• More casual than most Chelseas; you may prefer a more versatile model
• Some purists dislike the foam footbed
• Outsole is cemented to the midsole; pricier brands are sewn or nailed on
• Not ideal for hiking or dynamic movement (this is true of most Chelseas)

Overview: Thursday Legend Boots

• Unusual balance of sleek and casual
• Chunky, grippy sole
• Hardwearing casual leather

Chelsea boots stand out not just because they’re laceless but because, unlike moc-toe or logger boots, the Chelsea did not start out as a work boot — they were a walking shoe for Queen Victoria.

This is why you’re more likely to see Chelseas that are dressy, or at least smart casual. There are exceptions, but Chelseas never became all that popular as work boots or hiking boots not just because of their Victorian history, but because they just don’t secure onto the foot as well as boots with laces.

The Legend fills a gap in the market: it’s uncommonly grippy, tough, and casual, but the shape is also pretty sleek. It’s not often can you wear a Chelsea with a baseball cap, but these are casual without looking sloppy.

This balance is what makes the Legend stand out among Thursday’s boots: it has a refined, almond-shaped toe (less casual than a Blundstone), but also boasts a tough, grippy sole and high durability.

Leather: Thursday Legend Boots

• Low-maintenance “Rugged and Resilient” leather
• Waterproof suede available
• Scratch-resistant finish

The Legend’s toughness is underscored by its leathers. I got mine in what is Thursday’s bestselling leather overall: Black Matte.

It’s black, and it’s matte, so it’s subtle instead of glossy and doesn’t risk coming off as too dressy (like Thursday’s black Cavalier Chelsea) or military (like Doc Martens).

Thursday categorizes their leathers as “Classic” and “Rugged and Resilient”, which are tanned with extra oils and waxes to make them more waterproof (oil and wax are hydrophobic) and more resistant to drying out. The grain is also slightly corrected (buffed and smoothed), enhancing scratch resistance.

The trade off with these tougher leathers is that the color is less dynamic or dressy than the “Classic” ones.

Interestingly, the Legend is only sold in the more outdoorsy Rugged & Resilient leathers — in addition to a waterproof suede. None of those more delicate, scratch-prone leathers for this rugged boot!

Construction: Thursday Legend Boots

• Goodyear welted: makes them easy to resole
• Highly water-resistant

A key feature of Thursday boots is their affordability and modern style, which introduces many guys to traditional boots.

The Legend features Goodyear welt construction, making them easy to resole and highly water-resistant, unlike popular and simliarly-priced Chelseas from Blundstone or Doc Martens. (Doc Martens say they have a Goodyear welt, but because the outsoles are melted on with flame, most cobblers will refuse the job. But any cobbler can resole the Legend.)

Honestly, you probably won’t ever need a resole. The chunky Commando sole adds a lot of height, protection from the cold ground (it makes a difference in winter) and a lot of rubber to wear down. They call this sole the Storm King, and I wore another Thursday boot with that sole for over a year without losing even a smidge of the grip.

How to Style Thursday Legend Boots

• These are more casual than most Chelseas
• Classic workwear fabrics like denim, canvas, and flannel work best
• The big sole makes the Legends work well with straight or wide leg jeans

I need to write an article that’s just about styling Thursday boots, but the takeaway for the Legends is that they’re unlike other Chelsea boots and even unlike most Thursday boots. The brand is best known for the Captain, a sleek boot that looks better with tapered jeans than wide legs.

The same is true of most Chelsea boots; because it’s hard to make a slip-on, laceless boot that doesn’t hug the foot to keep it secure, Chelseas tend to be slim and they tend to be on the dressy side. (Yes, there are exceptions. That’s why I said “tend”!)

But the Legend’s chunky sole and casual leather make it work better with straight leg and relaxed fit trousers than most Chelseas. It’s still fairly tapered at the toe, but you get that extra versatility: the Legend is firmly a casual boot, but it can work with almost any kind of “casual.”

Because mine are black, I wear cooler colors with my Legends like black, gray, blue, white, burgundy. My favorite materials are natural ones like denim, canvas, wool, and leather. Try dark wash jeans with a flannel and a leather jacket, or chinos with a t-shirt and a denim jacket.

Sizing: Thursday Legend Boots

• Runs larger than sneakers (so size down)
• Free sizing exchanges from Thursday
• Low instep is fixable with tongue pads
• Wide widths available for some leathers

If you’re a 12 in sneakers, you’re an 11.5 in these boots. If your sneakers are sometimes 12 and sometimes 11.5, then you’re an 11 in these boots.

When compared to your Brannock size — your official foot size that you get on the measuring device in a store — Goodyear welted boots typically run larger than sneakers, which tend to run small.

In boots, a size 11 will fit an 11.5 Brannock, while a size 12 sneaker will often fit an 11.5 Brannock.

With laceless footwear like this, what’s important is the instep: the area on top of your foot near the ankle.

If your instep is low, like mine, then Thursday’s Cavalier will fit you better. The Legend fits the same as their Duke Chelsea, which was a little too roomy for my abnormally low volume feet.

But if that happens to you, you can do what I did: I picked up some Pedag suede tongue pads ($10) and stuck them under the instep part of the Legend, which made them fit perfectly. And I should really emphasize here: my feet are anomalously low volume, so this tip is probably not relevant for you.

Thursday’s Legend Vs Their Other Chelsea Boots

• Duke: Same fit, flatter sole, different leather options
• Cavalier: Dressier, slimmer fit, leather sole
• General Purpose: Rounder, wedge sole, premium Blundstone alternative
• Journeyman: High-end, whole-cut leather, premium internal components

Thursday offers four other Chelseas: The Duke, The Cavalier, The General Purpose, and The Journeyman.

Here’s how they differ to the Legend.

The Duke

The Duke is built on the same last as the Legend, so it shares the same fit and shape.

The main difference is the flatter sole, which is more versatile. But it’s also sold in different leathers, including “Classic” ones like a more glossy Black and my favorite, Honey Suede (pictured above).

This is one of the original two Chelseas in Thursday’s lineup, intended to be the versatile, all-purpose option.

The Cavalier

Since so many guys like dressing up Chelseas, Thursday made a dedicated model for them called the Cavalier.

The key differences are that it’s made on a slimmer last (I found it fit me better because I have a low instep) and it has a leather sole with rubber studs peeking through for extra grip.

Get it in Black for something you can wear with a suit or one in a more casual leather, like the Sandstone Suede I wore, for a versatile option that’s perfectly wearable with jeans.

The General Purpose

While the Duke and Legend are meant to be the casual Chelseas, Thursday released an extra casual one in 2025 called The General Purpose that’s something of a premium version of the Chelsea work boot.

It has a rounder toe and a wedge sole, but is made with a Goodyear welt and higher-end materials than the Blundstones it might bring to mind.

The Journeyman

Lastly, the Journeyman is the Chelsea in Thursday’s premium Black Label Collection. (I reviewed one of the other models, the Challenger, here.)

Pricing around $300, these are designed to appeal to the purists who don’t love the elements of Thursday’s designs that are intended to limit break in: the Journeyman has all leather internal components, plus they uppers come from world renowned tanneries like CF Stead. Expect less comfort out of the box, but more approval from boot hobbyists!

Thursday’s Legend vs Competing Chelsea Brands

Real quick, here are a few other Chelseas I’ve owned and how they compare to the Legend.

Thursday vs Blundstones ($199.95): “Blunnies” have a more casual, rounder toe shape and they’re built for shock absorption. They’re better at it than the Legend and they’re lighter as well — but they cost more and can’t be resoled.

Thursday vs Red Wing ($299.95): Red Wing Heritage sells the Classic Chelsea, which is Goodyear welted and made in the United States, unlike the Legend. The main difference is that it’s much chunkier, it has a flat wedge sole, and it’s $100 more expensive.

Thursday vs Meermin (~$270): If you’re attracted to that whole cut look, Meermin has some Goodyear welted Chelseas. The sole isn’t as grippy and functional, and they’re about $270.

Thursday vs Dr. Martens ($170): Dr Martens Chelsea’s are actually about 30 bucks cheaper than the Legend, but almost no cobbler will resole them, and the leather is both less versatile and lower quality.

Thursday vs Ariat: Lastly, Ariat’s Wexford costs about the same as the Legend and hits the same note of casual-versatile. It’s 100 percent waterproof, but it’s not resoleable.

But the Legends are waterproof enough. You can’t stand in a lake fishing with these, but when most guys say they want waterproof boots they really mean they want to be able to walk through puddles when it’s raining.

As you can see in this video, I’ve done that in my Legends and my socks stayed dry.

For almost anyone, Goodyear welt construction makes a boot as waterproof as they really need.

Wrapping Up

That’s my Thursday Legend review; I think we’ve covered just about everything you need to know about how they’re built, how to wear them, and some alternatives. Let me know how you like to wear these, and otherwise, check out more stuff on casual, durable menswear and footwear on our YouTube Channel.

---