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Home / Blog / Shoes

Thursday Boots Legend Chelsea Boots Review: Your New Go-To

Published on September 22, 2023 by Graham Romero · Product Reviews, Shoes May contain affiliate links (what's this?)

Here’s a pair of awesome Chelseas from Thursday Boots. Read on to find out why I love these boots!

Table of Contents

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  • Quick Take
  • Features and Construction
  • How To Style the Legends
  • Recommendation: Are They Worth It?
Thursday Boots Legend Chelsea Boots Review
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I’ve worn a pair of Thursday Boots Legends in the Bourbon color for almost a year now. Here’s what I think about them.

Here at The Modest Man, we love Thursday Boots. We’ve had a handful of team members review Thursday products, and they don’t disappoint. The Thursday Legend has become my go-to Chelsea boot. 

In this review, I’ll shed some light on why I love them!

Quick Take

The Legends are fantastic. They’re exactly what I’ve come to expect from Thursday Boots — high-quality boots that punch well above their weight class in terms of price.

Thursday Boots quality assurance

I completely recommend them if you’re looking for a pair of Chelsea boots that work well for casual and business casual styles.

Features and Construction

The Legends are Chelsea boots with the classic features you’d expect. They’re laceless and feature elastic sides and pull tabs that help you slip the boots on.

Thursday Boots Legend Side View

The pull tabs are very durable, and they feel incredibly sturdy. I haven’t had any inclination that they’ll ever rip off.

The boots are made of rugged leather and have a rubber outsole. The insole is shock-absorbing and anti-microbial. Another great feature is the cork midsole that conforms to your foot after you break the boots in.

Speaking of breaking in, the Legends were comfortable right out of the box. Like any boots, you need to wear them a bit before they conform to your foot, but I don’t have any complaints about the comfort of the Legends.

A notable feature of the construction of the Thursday Legend is the Goodyear welt construction. If you’re not keen on that term, just know that it means that these boots can be re-soled if ever needed. Don’t worry; they should last a long time before getting to that point. 

Thursday Boots Legend back

Thursday Boots can really take a beating, but you can rest assured knowing that if and when the time comes to replace that worn-down outsole, the Goodyear welt has your back.

How To Style the Legends

When it comes to Chelsea boots, you need to understand the level of formality of the pair you have. Some Chelsea boots are dress boots. However, the Legend is a casual boot.

When should you wear them? They’re suitable for any casual occasion and look nice enough to wear in business casual settings, too. For anything more formal than that, opt for a dress boot. 

In fact, the Falcon colorway of the Legend has a dressier look.

The Legends look great with jeans, chinos, or linen pants. Obviously, you wouldn’t want to wear them with something very casual and athletic like sweatpants. Otherwise, have at it! 

Thursday Boots Legend

As a basic rule of style, you need to make sure you’re wearing colors that flatter one another. The Legends come in some different colors, and luckily, they’re all neutral. 

I love the brown of the Bourbon ones I have. They’re classic, neutral, and earthy. They match literally everything I wear.

While they do look classic and stylish with dark or light-wash jeans, I typically opt for chinos. The boots compliment my navy chinos perfectly. Blue and brown is a classic, subtle, and masculine color combination.

They also look fantastic with olive and khaki. If you want to get more adventurous, style them with burgundy or other dark reds. They also look good with brighter colors; just don’t go too bright or the contrast of your pants.

If you want to wear them with black, go for it; just be intentional about it. Some people say that black and brown don’t go well together. However, it’s a matter of opinion.

If you wear the Legends with chinos and a button-up shirt like an OCBD, you’ll be dressed to impress. Outfits like that remain business casual but look very well put together. People will see you and think, “That guy dresses well,” and they’re right. You will be dressed well!

Thursday Legend boots
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I often wear these boots with chinos and a T-shirt. It’s a great, casual look. Remember, these are casual boots. You wouldn’t typically wear dress boots with a T-shirt, but casual boots are okay.

Recommendation: Are They Worth It?

Are these boots worth the $200 price tag? Yes. A resounding yes. 

Thursday Boots direct-to-consumer business model allows them to provide incredibly high-quality products for a low cost.

The Thursday Boots Legends look great in casual or business casual settings. They’re rugged and stylish, come in a variety of colors, and have a Goodyear welt.

There’s nothing else that I would ask of a $200 boot, and to be completely honest, I don’t have a single complaint with the Legend.

If you want a pair of Chelsea boots but don’t like the look of the Legend, be sure to check out Thursday’s other Chelsea boots.

What other Thursday Boot shoes or boots do you want us to review? Let us know in the comment section!

Product Reviews, Shoes Thursday Boots

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