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Men's Jesse Handcrafted Leather Cowboy Boots

STYLE # 55266
now $174.50 (was $349)
Available colors

Select Size View Size Guide
Sorry, this style is now out of stock.
  • Smooth cowhide leather boots
  • Burnished leather, calf leather lining, welt construction, leather pullstraps
  • 1.50" heel, 6" shaft, 12.50" circumference, 1.42 pounds


Top of the line in looks and construction, the sleek Jesse boots offer a dashing alternative to your everyday kicks. Crafted from smooth, burnished cowhide leather, they feature western yoke detailing at the front and slightly rounded toes, as well as durable leather lining and outsoles. With their contemporary seam details and sophisticated sheen, these ankle boots are one of a kind. With leather pullstraps for easy wear.

This boot is crafted with an intentionally unlined heel, which prevents socks from catching and heels from rubbing, enabling a more secure and comfortable fit.

Fit to size. For a wider fit, we recommend ordering 1/2 size up for more comfort.

Combining classic western style with fashion-forward design, these hand-lasted boots are crafted in the traditional way, piece by piece, from premium leathers. Featuring stacked leather heels and 100% leather piping, each handmade boot offers top quality, durability, and unique personality.

1.50" heel, 6" shaft, 12.50" circumference, 1.42 pounds
Made in:
Product Care:

Overland ships all orders free via standard ground shipping to all 50 states and APO/FPO addresses. For details on expedited shipping or for deliveries to US Protectorates, please refer to the Shipping page.

We want you to be completely satisfied with your Overland purchase. For your convenience, we provide free return shipping for orders within the 50 states, with a prompt exchange or refund process. For more details, visit our Returns & Exchanges page.

Our Customer Service team will be glad to assist with any questions. We are available 7 days a week at 1-800-683-7526 or by email at [email protected].

Overland welcomes international orders. Depending on the order and destination, additional payment requirements may apply. Please refer to the International Orders page for more detailed information.


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Reviewed by 12 customers
10 of 12 reviews
MR A from Cornwall ny
May 1, 2022

Great boots very comfortable

5 5
Good quality at a great price
MK from Vermont
Jan 22, 2022

Great products with very good quality.

5 5
Everything I have bought from Overland has been fantastic, of high quality and priced well.
Linda from Buffalo New York
Jan 21, 2022

Gorgeous boot!

5 5
The leather was impressive. I really loved the sheen. It looked like quality of long ago. I was sad that they did not come in a wide with for my son. They were a regular width for the majority, but my son needed a wide to be comfortable. Since this company has a limited line of super good product, I am suprised that wider widths are not offered.
Ernie from Westminster, CO
Jan 18, 2022

I bought a second pair right away, because I love them.

5 5
I use them for dress and casual wear. The leather is so soft. They are so comfortable since the day I first tried them on. I get a lot of complements on them. They are son elegant.
Ernie from Westmister, CO
Jan 18, 2022

I bought and second pair right away in a different color.

5 5
I use them for casual and dress. I love the fact that I could not believe how comfortable there are from the first time I wore them.
Lisp from Massachusetts
Dec 30, 2021

Well made quality leather

5 5
Unfortunately these boots were too small for my husband One he was able to get on and the other one he was not! The pointy toe seem to be the problem.
Ikanik from Monrovia, CA
Dec 21, 2021

Great pair of boots with a nice western touch.

5 5
A great pair of boots. They were made of very soft and good quality leather. On top of everything, they are very comfartableto wear. I am very happy with this purchase. My hard earned dollars were well spent!
Jim The Runner from Florida
Dec 20, 2021


5 5
Had to size down from my usual 9.5 in shoes to an 8.5 & they fit perfectly
Jake from Houston, TX
Nov 12, 2021

Incredible, be aware of sizing!

5 5
I'm a boot guy and have rotated through owning and thrifting off a ton of TAFT, Thursday, Tecovas, etc. This is the best black boot I've come across. Classic silhouette that sits perfectly between the Cowboy Boot (can't wear slim jeans) and the Chelsea Boot (can't get respect in Texas). Wears in well, unassuming, and unquestionably cool. My only note is the sizing. I typically wear an 11 in sneakers / TAFT / Thursday. The 11 in these was huge, so I exchanged for a 9.5 (what I wear from Tecovas), which fit perfectly.
Barbara from Magnolia, Tx
Sep 9, 2021

Too small

5 5
These boots are beautiful but too small for my husband. He really needed at least a 14. We were very disappointed but had to return them. Any thing Overland puts out is high quality. I would highly recommend these boots.

Our Values

A lot has changed since our humble beginnings in Taos, NM, more than 45 years ago—but the core values of our family business have always remained the same. Now, as then, we're dedicated to bringing you heritage-quality products expertly crafted from the world's finest natural materials.

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