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New Boot Drop: Week of October 16th, 2023

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: Mar 20, 2024
8 min read
Watch the New Boot Drop for October 16th-22nd on YouTube

Welcome to a fresh edition of boot drop: I’m covering all the latest heritage style and boot releases for the week of October 16th through the 22nd. 

I don’t know about you, but once I feel the cool autumn air, I have an insatiable urge to eat pie. I’ve been eating pie every day for the last 10 days. It’s insane. 

Let’s talk new boots. 

New Releases: October 16 – October 22, 2023

Oak Street Bootmakers

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Oak Street just put out a new limited edition beauty. This one was a pure passion project for them, as they really just wanted to make a boot many of the staff wanted to wear. 

Turns out, that philosophy makes for some awesome boots. 

They just released a cap-toe Field Boot in Maryam Toscanello Horse Rump with a Dainite Ridgeway sole, a 270-degree Goodyear welt, and freehand brogue details. 

I don’t have any experience with Horse Rump leather, though my Instagram feed is basically constantly filled with it. That’ll probably end soon, though if I’m honest, I’ll probably test out an Indonesian bootmaker before I pick up another boot from Oak Street. 

That said, this is a tasty looking boot. 

Not that anyone asked, but I feel like this is a good time to express my displeasure with the Dainite Ridgeway sole. It’s great for traction, but why does it look like that? I’m not a fan of the tread pattern. Not that it really matters. 

All in, Oak Street’s new limited release is a great looking boot and is going to make some folks very happy 

Truman Boot Co. 

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Truman also released a stunner of a new boot. I’m stoked on this one. 

It’s an unstructured plain toe boot with Dark Coyote Seidel roughout leather on a regrind sole. It’s built on their 79 last, which I absolutely love – I think it’s the perfect balance between the slimmer dressier brands like Thursday, but it’s not all bulbous and chunky like a Red Wing. 

And with the unstructured toe, it’s going to deflate a bit and really start to take on the owners character. Really, that’s all many of us want from a pair of boots: something that gains character as you wear it. 

Well this boot is going to have all kinds of character when you also factor in the roughout. 

Truman also says they have a structured cap-toe version with a honey commando sole coming next week, but I can’t think that far ahead—nor do I even want to with a boot that looks this good. 

Thursday Boot Co. 

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Thursday just released a Black Matte Stormking Captain. Given that the Captain is their most popular boot, and Black Matte is one of their most popular leathers, this mainly just surprised me that it didn’t already exist. 

I say we add this to the list of boots that absolutely demolish Doc Martens.

Speaking of…


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Unmarked just launched a new style they’re calling their Riot boots

You can think of these as high-end Docs that you can actually wear for more than a year. Or you can think of these as another great pair of boots from an innovative brand.

These are made with black bison leather, which Unmarked must have gotten a big batch of, because two weeks ago, they were on the “new boot drop” with a different black bison release. 

These Riot Boots have a bright orange stitch around the welt, though the pictures on Instagram really make it look yellow. I was looking at their product page, and it seems like a definitely BootSpy orange. 

In any case, it also features a storm welt and a chunky Vibram wedge sole. These look comfortable and ready for any type of weather. 

Grant Stone

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Grant Stone recently teased the release of a new Chelsea boot for the ladies. I’ve always been a bit shocked at the lack of high quality welted footwear for women, so any new release on this front is welcome. 

Helm Boots

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Helm just launched the Calistoga boot, which is sort of like a high top, moc toe, wedge sneaker boot. Makes sense, yeah? 

This blake-stitched baddie is inspired by wine country, though I don’t really know what that means. As far as I can tell, 100% of winery workers wear Blundstones. 

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Helm are always super comfortable and their leathers are solid. 

Taylor Stitch

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Taylor Stitch just dropped their Bomber Jacket in a cotton moleskin fabric. 

When it comes to a simple autumn jacket, a Bomber is hard to beat. It pretty much goes with everything. And it can look especially upscale with the right fabric. 

This moleskin fabric is the right fabric. 

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And if you’re feeling a bit more relaxed, like you want to sit on a windswept beach with a coffee mug, squinting into the distance, then check out the new Carson jacket from Taylor Stitch, a reversible fleece that’s all weather protection on one side, and all fuzzy sheep on the other. 

That fleece on the outside thing: I thought that trend was going to die, but it keeps on living. It’s growing on me for sure. I’ll probably get something like this the moment it stops being fashionable. 


Huckberry just did a full restock on all their waxed canvas jackets in all colors. You can find unlined, flannel lined, and wool lined versions of their super popular Trucker Jacket. 

Plus, they’ve got some incredible leather jackets, too, including a suede trucker, which is the coolest style ever. 

Unfortunately, suede trucker jackets all seem to start at $1,000 and I still don’t have the guts to drop that much coin on a single piece. But when I work up the courage, a suede trucker jacket is the business. 

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Huckberry also released their collaboration with the Grateful Dead

I had a roommate in college—still one of my best friends—but he’d play Grateful Dead on his guitar for like 8 hours a day every day. So seeing this collection just triggered my PTSD, so I can’t bear to look at this collection. Get it out of my sight. 

Standard and Strange

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Standard and Strange just dropped a triple-boot-whammy with Rolling Dub Trio.

First up: the Griffin Engineer in Dark Beige Suede. Whew, those are patina monsters if I ever saw ‘em. 

This engineer is built on a modified Munson last, so it’s a bit roomier in the toe box, and the leather is Japanese, though I’m not sure about the tannery. 

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Not only that, but you can find a Rolling Dub Trio Griffin 8.5” Plain Toe in Italian Horsebutt leather. This is built on the same last as the Engineer and has a similar shape through the vamp and heel. 

Of course, it’s a big ol’ lace up boot instead of a pull on, but otherwise, a very tasty looking boot. 

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And then to round out the triple-play, Standard and Strange is also carrying the RDT Forester II boot, which is a chonky beast of a boot. 

Made with the same Dark Beige Suede as the engineer, this has a brogue cap toe, fringed kiltie, an absolutely gigantic leather midsole with a foam wedge and a Vibram honey commando sole. Note the Norwegian welt in the front of the boot, too. 

Division Road

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Division Road has a full stock of new releases from Momotaro Jeans

Not going to lie, I don’t know a ton about denim, but I’ve heard about Momotaro several times, so I’m assuming this is a good thing. 

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Also at Division Road, a new Crockett and Jones collab is live, with three limited edition collared boots. If earlier we were talking about boots that make Doc Martens irrelevant, well, these make Timberland’s irrelevant. 

I’ve never tried an English boot, but I’ve heard nothing but great things about Crockett and Jones. I’ll have to give them a shot one day. One day. 

Hiroshi Kato

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Hiroshi Kato just dropped their new Anvil Jacket in Melton wool. This stuff is weatherproof and looks fantastic. 

This is going to be a great outer layer to throw on throughout fall and winter, so if you want to get ahead of the season, this is a solid choice. I’ve only ever tried one pair of jeans from Kato, and while I loved them, I also got really into boosting my squat weight at the same time, so I could only wear the jeans for like two months before my legs were too big for them. 

I might try one of their denim jackets next though because those look sick. 

Iron Heart

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And if you’re serious about giving winter the what-for, then check out Iron Heart’s new Whipcord N1 Deck Jacket in black. Iron Heart promises to release more Deck Jackets throughout fall and winter, so you might want to hold off if you’re looking for an olive jacket—or am I just projecting?

This is a powerful looking jacket, though I know with that fuzzy collar, one of my two dogs is going to make this coat its prison-cell partner. 

See You Next Week for All the Latest Releases

Last hot tip I have for you: get apples right now. This is the only time of year where biting into an apple isn’t an immediate disappointment. 

Thank you for checking out the week’s latest boot releases. 

To get the New Boot Drop every week, make sure to join over 5,000 guys and subscribe to Heritage, the only newsletter dedicated to men’s heritage fashion. 


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