Moc Toe Boots Compared: Red Wing vs Thursday vs Thursday Black Label

As the two most popular American boot brands, I’m always asked to compare Red Wing Heritage and Thursday Boot Company. (In fact, I already did a comparison of their bestselling cap-toe boots, Red Wing’s Iron Ranger versus Thursday’s Captain.)

But moc toe boots are a different beast: more chunky and roomy, more bouncy thanks to those wedge soles, and above all: more easily worn with modern wardrobes. Moc toe boots are the boot of choice for guys who want to avoid the vibe of the old timey work boot.

After several years of wear, I know these boots intimately — so let’s get started.

Why and How I Compared These Three Boots

Like I said at the start, these are the two most popular brands in America for casual, resoleable boots. There are arguments that the moc toe is the most noteworthy kind of casual boot: when I interviewed Red Wing employees, they said the moc toe was the best Red Wing boot and the one that best embodies the brand.

Thursday Boot Company disrupted the whole boot industry when they figured out how to make resoleable boots for under $200, and they’ve been eating into Red Wing’s market share ever since. There are reasons for the price difference, and I thought it was important to write this comparison to explain why.

Finally, I thought this comparison would be a good excuse to take a look at Thursday’s Black Label Collection, their extra premium lineup that was made to appeal to the most discerning of boot enthusiasts. Those sorts of guys take issue with the common features among Thursday boots that keep the price so low — but the Black Label boots (like the Builders) may be able to refute them all.

So this comparison isn’t just Red Wing versus Thursday. It’s a look at three distinct tiers of boot quality and what actually changes as you move up through them.

What These Boots Have in Common

• Resoleable
• Casual
• Appropriate for wet weather
• Good value
• Comfort improves with wear
• Cool (of course that’s an objective term)

You won’t go wrong with any of these boots. Unlike my comparisons of, say, Red Wing and Dr. Martens, there’s no clear loser here: it mostly depends on what you value.

All three are longlasting, water resistant, can be resoled, and will look cooler and get more comfortable as they age. These are the core strengths they all share, and they’re the most important qualities to look for in boots.

One last note: because they’re all moc toes with white wedge soles, all three boots are very casual. Unlike, say, Thursday’s Captain, they can’t be dressed up to business casual, but they work better than the Captain with loose jeans and streetwear.

Why You Should Choose Red Wing’s Classic Moc ($330)

• Biggest advantage: Made in USA
• Well priced (compared to other American-made boots)
• Unmatched in its influence and popularity
• The most leathers and colors to choose from
• Good all rounder

Instead of writing long paragraphs about each brand’s history and philosophy, I’m just going to tell you the reasons someone might land on this boot.

Value

For a lot of guys, Red Wing is the first resoleable boot they buy — it was for me! And while it took a while to get my head around the price tag, I’ve since learned after investigating a lot of American made boots that Red Wing is actually very well priced for an American-made boot.

This is because of the relative size of the company and the fact that they own their own tannery, which also gives them great quality control.

Made in America

Unlike the other two boots, this one is still made in the United States, and it’s made by an independent company with over a hundred years of history.

That’s the kind of story a lot of guys want for their boots, particularly at this pricepoint.

Leather Quality and Variety

Thursday usually has more leathers to choose from with their boots, but not in this case: Red Wing currently offers over ten leathers to choose from, and they’re always developing new ones to release each season.

Red Wing owns the S.B. Foot tannery, which isn’t just an arm of the brand: they’ve become world renowned for their quality and can be found on some of the most niche and expensive brands in the industry. See my look at Iron Boots or this cowboy boot collection for examples of great S.B. Foot leather that you won’t find on any Red Wings.

Cultural Influence

Red Wing is the reason why the orangey moc toe boot is such a popular style: they invented it. Whenever any other brand releases a moc toe, whether it’s Thursday’s Diplomat or Grant Stone’s Brass Boot, they always make sure there’s an orange one.

The Classic Moc is also a mainstay in pop culture, as shown in my banger video above about movies that have featured Red Wing boots. They simply run this category the way Chuck Taylors run cheap sneakers.

Old Fashioned Construction

All of these boots can be resoled, but there’s a case to be made that Red Wing’s is the best balance of classic and comfort.

Boots made with Goodyear welt construction are the easiest to get resoled (not the case for the Builder) and boot enthusiasts usually prefer a stiff, thick leather insole for the way it conforms to the foot’s shape over time (not the case for the Diplomat).

I can attest to this: as my first boots, I’ve worn my Red Wings more than the other two brands, and the footbed is shaped just like my foot now, and I loved that it remained that way even after I resoled them with cobblers Trenton and Heath (video above).

Just note that of the three boots, Red Wing had the toughest break in. It took me about ten wears before they stopped giving me blisters.

Why You Should Choose Thursday’s Diplomat ($199)

• Biggest advantage: Lowest Price
• Also the least expensive good moc toe boot you can buy.
• Comfort: the only boot here with no break in
• The most lightweight, flexible, shock absorbent, and sneaker-like
• Most versatile option, thank to the slimmer look and the option of two soles

There are a lot of reasons beyond the pricetag that have made Thursday the most talked about boot brand.

Value

At $199, the Diplomat isn’t just the cheapest of the three boots I’m comparing — it’s the cheapest good moc toe on the market. I’ve looked at all the other brands around the $200 pricepoint and none of them come close to this quality. It’s just as resoleable and water resistant as Red Wing but it’s over a hundred bucks cheaper.

And listen: that will cinch it for most guys. The average dude just wants a boot that looks cool, endures bad weather, and can last a long time. The Diplomat hits all those notes at a lower price than anyone else.

Comfort and Break In

Largely due to the thick leather uppers and thick leather underfoot, most boots give you blisters and sore feet when they’re new because the leather first needs the heat and friction of wear to soften and conform to your foot’s shape.

Thanks to slightly softer uppers and the use of foam footbeds over leather, this is the only boot that didn’t give me a tough break in. I can’t guarantee that you’ll have the same experience, but I’m comfortable saying that the Diplomat is the least prone to a tough break in.

I think Thursday Boot Company’s success has a lot to do with making their boots feel closer to a sneaker than their competitors: in addition to the lack of break in, the Diplomats are lighter, more flexible, and more shock absorbent than the other two.

With that said: when I’m comparing a brand with Thursday, the Thursday usually has a very decisive difference in shock absorption because of the foam insole. In this case, that insole is still an important differentiator, but we should remember that the Classic Moc and the Builder still have soft rubber outsoles. So the difference in rebound and shock absorption is there, but it’s not quite as impactful. (So to speak!)

Versatility

Most of Thursday’s boots have a more slim and low profile look than the industry’s voluminous, old fashioned, work boot-inspired models.

That slight sleekness means they’re easier to wear with slim or tapered pants, and they simply fit into a modern wardrobe more easily than its chunky ancestors.

All three of these boots are definitely casual, but the Diplomat is still the most versatile. Perhaps this comes down to it being the least conspicuous.

Why You Should Choose Thursday’s Builder ($349)

• Biggest advantage: Most premium materials and construction
• Made with leather from the world’s most celebrated tanneries
• Only boot here with all leather internal construction
• Stitchdown construction is less common and favored by many enthusiasts
• Easier break in than Red Wing despite containing more leather

I’ve been blogging about boots for almost a decade, and while the Diplomat is the most accessibly priced moc toe boot of note, there’s a case to be made that the Builder is the best value.

Highest Quality

Boots like these, which I’d put in the “made for enthusiasts” category, usually cost hundreds of dollars more. While the Builder is made in Mexico, I’m counting other brands that are made in Mexico and occupy a similar level in the industry, like Unmarked.

It remains true that all three of these boots do everything that most guys want their boots to do. I’m aware that the average guy won’t be convinced to pay the extra for the Builder, but I’ll still try to convey why a lot of people are really excited about this “Black Label Collection.”

Every kind of product seems to eventually get a community of people who love it so much it becomes a hobby. These kinds of guys, of course, are hardest to please, and they were enraged by the foam insole and lighter, non-traditional build of boots like The Diplomat.

If asked, said boot nerds will list their favorite tanneries for boot leather and those are the tanneries used on the Black Label Collection. Mine have the world famous waxed suede called Rambler, made by the undisputed masters of suede: England’s C.F. Stead (I totally visited them).

All Leather Internal Construction

In addition to the fancy uppers, there are a few other elements that please the purists.

One is all leather internal construction. That means no foam footbed like on the Diplomat, but even Red Wing doesn’t manage to meet this mark: like most boots, they use a plastic impregnated fabric called celastic (a.k.a. thermoplastic) to shape the toe.

Some guys prefer all leather construction because it’s more old fashioned, some think it molds better with wear. The average guy won’t notice any difference, but it’s still true that it’s an impressive feature that’s usually only found on much pricier boots.

Stitchdown Construction

All three of these boots are resoleable, but the Builder is made with a more unusual form of resoleable construction called stitchdown.

I’ve asked a hundred bootmakers if there’s a difference with regard to durability or water resistance or anything else, and the answer is: not really. But as you can see in the video above, boot enthusiasts tend to prefer stitchdown construction: it usually requires more skill and it’s harder to fake.

Meanwhile, although any neighborhood cobble can resole a Goodyear welted boot, it’s harder to find one who can resole a stitchdown boot. It’s absolutely possible to find one, but you’ll need to call ahead to make sure he’s got the machinery.

Pretty Comfortable

Usually, the more leather a boot has, the harder the break in. Despite that, the Builder was easier to break in than the Red Wing.

This is because of some impressive engineering feats like using extra soft vachetta leather for the insole and cutting channels into the midsole (shown above) to improve its flexibility.

The first couple of times I wore the Builders, I certainly got sore feet. But they became easy to wear much more quickly than the Red Wings. (But yes, the Diplomat still wins in the ‘break in’ category.)

Red Wing vs Thursday Sizing

• All my sneakers are 11.5 or 12
• My “true size” on the foot-sizing Brannock device is 11.5
• Red Wing Classic Moc: 11
• Thursday Diplomat: 11
• Thursday Builder: 11.5

I think about half the guys who wind up on articles like this are trying to work out what size to get.

This might be your first pair of real boots, so here’s something important: your boot size is usually not your sneaker size.

Before you buy boots on the internet, find out your Brannock size. That’s the device they use to measure feet in the shoe store. Go and pretend you want to buy new shoes so you can get your Brannock, or “true size.” Mine is 11.5.

Sneakers are often half a size larger than your true size: maybe half of mine are size 12.

My typical boot size is 11. That’s my size in the Red Wing Classic Moc, the Thursday Diplomat, and most of my other boots.

But I’m 11.5 in the Builder.

There’s a decent chance this is because the Builder is stitchdown and the others are Goodyear welted: I’m 11.5 in Red Wing’s stitchdown boots too.

Red Wing vs Thursday: The Fit

• The Diplomat is the closest to a sneaker in terms of comfort (weight, rebound, break in, etc)
• The Builder has an easier break in than Red Wing, despite having more leather

The Red Wing and the Builder both have that classic, voluminous moc toe fit: high side walls and roomy toe boxes to allow for dynamic movement and thick socks.

Besides having an easier break in and even though the Builder is a little roomier, I don’t think many guys will notice a difference in fit between the two.

The Diplomat, meanwhile, is so popular because it’s sleeker than the other two. My toes don’t feel cramped, but you do have less room. If you want that roominess, you have the option of wide sizes or sizing up 0.5 with the Diplomat — or you can pick one of the other boots.

Red Wing vs Thursday: The Comfort

It’s pretty much impossible to definitively say one boot is more “comfortable” than another, because there are so many different ways that guys understand “comfort.” I did this article on the most comfortable kinds of boots where I explain more, but to keep us relevant to this article I’ll say the following.

The Sneaker Kind of Comfort

If you’re used to or prefer the feeling of sneakers, you’ll find the Diplomat the most comfortable: it’s lighter and easier to break in.

The Boot Kind of Comfort

Mostly because they have thick leather insoles, the Builder and the Classic Moc do a better job of conforming to the shape of your foot with time — and for many guys, that’s what they love about boots over sneakers.

The Builder is more comfortable than Red Wing in that it’s more flexible and has less of a break in.

The Shock Absorption

Usually, the foam insole makes Thursday’s $199 boots vastly better at shock absorption than their pricier and more old fashioned competitors. But since all three of these boots have spongy rubber outsoles, that particular difference isn’t huge.

Red Wing vs Thursday: The Waterproofness

One last question that comes up when comparing these brands is waterproofness. This is because Red Wing and Thursday tend to be the first high quality boots a guy buys.

So here’s the simple answer: yes, all three boots will keep your feet dry when it’s raining.

What I did not just say is that they’re “waterproof”, which is a technical term meaning that you can stand in a pond all day.

But practically every time a guy asks if a boot is waterproof, he means that he doesn’t want to have to hop over puddles when it’s raining or snowing. I can say from experience that all three of these boots perform as well as each other.

Some guys argue about whether stitchdown or Goodyear welts are more waterproof, but the answer depends on a lot of other factors that go into the boot you’re talking about, and the practical takeaway is always the same: neither is waterproof, but both will get you through a rainstorm.

Conclusion

One last time: all three boots can be resoled and will last for ages, get more comfortable with wear, endure bad weather, and look cool with casual outfits.

Pick the Diplomat if you want to spend the least amount of money, get the most versatile boot, or have the option of a lug sole.

Pick the Red Wing if you want an icon of American craftsmanship or the widest array of leathers.

Pick the Builder if you want to wear boots made with leather and construction that embodies the highest level of skill.