Design 
Quality of Materials 
Craftsmanship 
Fit & Sizing 
Value for Money In high school, I remember working through summer and winter breaks on odd construction jobs.
I was always the young rube—a hired hand amongst jaded older guys. And true to my position, I would often show up in a pair of thin canvas Vans. The other guys would proceed to roast me for being such a rookie.
I took note of their boots—usually some kind of beefy moc toe. I tried the style, but they looked comically large on me.
Now that I’m a jaded older guy myself, I’ve been diving back into the style. With the cooler months on the way, I decided to pick up the most stylish moc toe I’ve worn to date: the Thursday Diplomat.
While it’s the most stylish, that doesn’t mean much if it’s not going to last.
So what’s the Thursday Diplomat really like? Keep reading to find out.
A Quick Overview of the Diplomat
The Diplomat is a Thursday Boot Company original. I didn’t realize this, but the Diplomat launched at the same time as the brand’s famous Captain and President.
While it’s never quite reached the same heights as the Captain or President, it’s been a staple for Thursday since the beginning.
The Thursday Diplomat is a unique take on the classic moc toe style. Moc toes have the unique U shaped stitching along the toe box, and they’re known for being robust boots.
Some of the most popular versions are the Red Wing Classic Moc Toe and the Thorogood Moc Toe.
While Red Wing and Thorogood are praised as hard working boots, the Thursday Diplomat boasts a much slimmer, more style-forward silhouette.
Things to Consider Before Buying
Moc toe boots historically have been seen as work boots.
The Thursday Diplomat isn’t a work boot.
It’s meant for guys who like the workwear aesthetic, but find that the traditional offerings from Red Wing, Danner, and Thorogood are way too bulky in the toe.
Thursday Boots are designed for guys with a more modern, slim fit style. Not to spoil my whole review, but while the Diplomat is a fashion-forward boot, it’s also comfortable, durable, and built well.
The Thursday Boots Diplomat is a one-of-a-kind moc toe. Most comparable boots have a huge toe box that doesn’t work well with a pair of fitted jeans or chinos. Combine a slim design with high quality materials like a Vibram Christy wedge sole, steel shank, and Thursday’s excellent oil-tanned Rugged & Resilient leather, and you’ve got a winner here.
My Hands On Review
First Impression
Of all boot brands, I think Thursday Boot boxes smell the best. I just have to put that out there.
Opening up the Diplomats, I knew they had a lower profile than the Red Wing Moc Toe that I’d been wearing, but I was shocked at just how much slimmer these boots are.
The Diplomat is a fashion-forward work boot. What I mean by that is: it’s got a classic American workwear look, but it fits much better into a modern guy’s wardrobe.
Still, it’s important to note that the Diplomat has a 360-degree Goodyear welt just like it’s more workwear focused competitors. This Goodyear welt helps a ton with weather resistance and also leaves the opportunity to recraft your boots if the sole wears down.
If you wear slim fit jeans with more taper below the knee, the Diplomat is the only moc toe boot that looks aesthetically pleasing.
As a point of reference, I’ll be discussing Red Wing a lot, because the difference is striking (but I also really like the Red Wing for what it is).
The Red Wing Classic Moc just doesn’t work with my slimmer fit jeans. I have to wear my jeans with a wider leg opening so that they don’t end up looking like clown shoes.
But that’s not the case with the Diplomat. On the other hand, I think regular fit and less tapered jeans sort of swallow the Diplomat up, so I think you almost have to have a slimmer fit style to pull them off.
Leather Quality and Care
At the time of writing the Thursday Diplomat comes in five different leather options, four of which are in Thursday’s Rugged & Resilient line.
I picked up the Burnt Copper, which is the most popular version of the boot.
All Rugged & Resilient leathers are oil-tanned and have a very matte appearance. I also have the Captains in Arizona Adobe and the Presidents in Tobacco, so I’ve had experience with this type of leather and know how it ages and patinas.
I’m a big fan of the Rugged & Resilient leather. It’s tough and very water resistant, which makes it an excellent option for an everyday boot.
I think the Rugged & Resilient leathers fall a bit short on versatility. They’re not quite as dressy or classy as Thursday Chrome leathers, and they tend to look fairly worn-in immediately.
Some guys love the look of a well-worn pair of boots, and if that’s you, you’ll love the Rugged & Resilient leather. Within a few days, it looks like you’ve owned the boots for years (though they won’t deflate and look all creased and crummy—they stay in shape really well).
I treat my Thursday Rugged & Resilient leathers with Bick 4. It doesn’t darken the leather and it doesn’t penetrate super deep into the leather, so you may want to do a few layers.
Bick 4 is an outstanding addition to your leather conditioner collection. It’s inexpensive and perfect for giving your boots a pick-me-up without changing the color at all. It doesn’t penetrate deep into the leather, so you should use a liberal amount, and you may want to do several layers, but the price is right.
But because the leather is already packed with oils and waxes, it really doesn’t need much care at all. I just recondition every six months or so to clean up my boots and get them looking closer to new.
Sole
The Thursday Diplomat features an American Vibram Christy sole. Like you’ll find on most moc toe boots, the Christy is a white wedge sole.
Wedge soles offer a lot of support for guys who stand on concrete all day, and they’re especially slip resistant if you’re working in a shop where stray oil slicks are present.
One downside of wedge soles is that the big brands (Red Wing, Thorogood) don’t have any shank.
The Thursday Diplomat does feature a steel shank, however, and the added arch support is welcomed.
Of the three moc toe boots I own, I think the added support makes the Diplomat the most comfortable.
The insole is an anti-microbial Poron, which is quite soft and padded, and the midsole is made from leather and natural cork. The leather and cork midsole takes a little time to break in, but it compresses and condenses slower so you get more life from your boots over the years.
I definitely prefer the leather and cork midsole over synthetic, as synthetic midsoles tend to just deflate after a certain amount of miles. While the break in takes a little longer, the durability is vastly greater.
Fit and Sizing
The Thursday Diplomat comes in a wide range of sizes, from 6-16, with half-sizes in between.
Thursday’s boots fit similarly to most other boot brands—you should order a half-size smaller than you would in sneakers.
So I’m normally a size 10.5 in sneakers, and I get the best fit with a Thursday size 10.
I also wear a size 10 in Red Wing, Grant Stone, Wolverine, Thorogood, and pretty much every other respectable boot brand I’ve tried.
Unlike other moc toes, the Diplomat doesn’t offer a ton of room in the toes. They fit pretty much exactly the same as my Captains and Presidents—a touch narrow in the toe, but secure in the heel and no rubbing along the instep.
Break-in Period
The break-in period takes a little while—longer than most other boots I’ve worn. The Rugged & Resilient leather is quite stiff, which isn’t a bad thing, but the first few days can have you feeling like you ordered too small.
I knew to expect this from my Arizona Adobe Captains and Tobacco Presidents, so I wasn’t worried when my Burnt Copper Diplomats had my feet aching a bit.
I didn’t get any blisters, but both my heels were tender and the boots did a fair amount of squeaking in the first 10 miles of wear.
After 10 miles though, the heels started to stretch and the whole boot became more comfortable.
I recommend wearing your Diplomats with a thick pair of wool socks, at least for the first 10 miles of walking. While it may feel a little snug, you’ll protect your feet and break the boots in faster.
What do Other Reviewers Say?
At the time of writing, the Diplomat is rocking a 4.9-star rating with over 1,200 reviews. Guys say they love the workwear vibe and slimmed down shape.
I wasn’t the only one to have a little trouble with the break-in—others had similar reports, but of the reviews I read, no one felt the break-in was too much to handle.
It says something that many reviewers were buying the Diplomat as their second or third boot from Thursday—the brand has high marks for their customer service.
Thursday Boots Diplomat Alternatives
Red Wing Classic Moc Toe
The Red Wing Classic Moc Toe is the most popular moc toe in the world. It’s the boot that put the style on the map.
Of all the alternatives listed here, the Red Wing has the tallest toe box. I own it in the Slate Muleskinner leather (review here), and I’m a big fan of how rugged and durable this boot is.
I’d pick the Red Wing Classic Moc over the Thursday Diplomat if you prefer your boots American-made and you wear regular fit jeans with a wider leg opening.
That said, they cost a bit more, and I wouldn’t say the quality is substantially better—it’s more of a “country of origin” type thing.
The Red Wing Classic Moc Toe boot has quite a large toe box, which can be off-putting for some, though it’s an ideal match for American Heritage workwear aesthetic. The Puritan Triple stitching, 360-degree Goodyear welt, and thick full grain leather footbed all make for a beast of a boot that will easily last years.
Thorogood Moc Toe
If you’re looking for a moc toe boot for work, I’d pick the Thorogood Moc Toe.
It’s also made in the USA, and it’s my top work boot choice because it’s relatively inexpensive (but still a little more than the Diplomat), tough, and I don’t mind beating it up.
Like the Red Wing Classic Moc, the Thorogood Moc Toe has a tall profile and doesn’t fit aesthetically with a slimmed down modern style.
The Thorogood Moc Toe is an excellent value buy work boot. While I don’t think it’s as stylish as other alternatives, lightweight features like a fiberglass shank and Poron insole boost the rugged durability while cutting cost and weight. If you’re looking for a relatively inexpensive moc toe work boot, the Thorogood Moc Toe is my top choice.
Grant Stone Brass
The Grant Stone Brass boot looks different than the other options here—it has a heavy rubber lug outsole as opposed to the wedge sole most moc toes feature.
Compared to the other boots, the Brass is much more expensive. But it’s also at the high end of quality.
If you’re looking for a versatile moc toe and your priority is quality over budget, then you’ll love the Grant Stone Brass.
The Grant Stone Brass boot is a total beast. The construction and stitching is meticulous and the build quality is the best I’ve experienced. While I personally prefer a slightly slimmer style, there’s no denying that the Grant Stone Brass Boot is one of the best value-offers in boots today.
My Overall Thoughts
What I Like
The Diplomat is a slimmed take on the classic American heritage moc toe style, which makes it the ideal option for guys who wear more modern fitted jeans.
There are a ton of sizing options, from 6-16.
Of all the moc toe boots I’ve worn, the Diplomat has the best arch support because of the added steel shank.
The Vibram Christy wedge sole balances durability, grip, and shock absorption.
What I Don’t Like
There are no wide sizes available (E-EEE).
Who is the Thursday Boots Diplomat for?
The Thursday Diplomat is an excellent boot if you love the moc toe style, but haven’t been able to find a version that looks good with your slim fit jeans.
The Verdict
While I’ve pegged the Thursday Diplomat as a fashion-forward boot, it’s important to note that the quality and construction are fantastic for the price.
It’s a sturdy boot, no doubt. I just think that the biggest reason to buy the Diplomat over any other moc toe boot is that it has a much slimmer, more modern silhouette.
I really like the Rugged & Resilient leather—it doesn’t take long until the boot starts to look like you’ve owned it for years. It’s packed with oils and waxes so the leather doesn’t need much upkeep and it has plenty of weather resistance.
The steel shank makes the arch support better on this boot than any other moc toe I’ve worn.
Overall, I’m really happy with the Thursday Diplomat, and I’ll be rocking it through the colder months for years to come.
The Thursday Boots Diplomat is a one-of-a-kind moc toe. Most comparable boots have a huge toe box that doesn’t work well with a pair of fitted jeans or chinos. Combine a slim design with high quality materials like a Vibram Christy wedge sole, steel shank, and Thursday’s excellent oil-tanned Rugged & Resilient leather, and you’ve got a winner here.
FAQs
Which is better: the Thursday Diplomat or Red Wing Moc Toe?
I like the Thursday Diplomat better for style because of its slim silhouette, but I would rather work in the Red Wing Moc Toe because of the sturdy toe box and extra room.
What does “moc toe boots” mean?
Moc toe boots refer to the construction of the toe box. They’re sewn like moccasins in the toe, which creates a unique U shape along the upper.
Who invented the moc toe?
Red Wing created the first moc toe boot in 1952 and the style has been popular with construction workers and hikers ever since.
