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Men's Isaiah Leather Shoes

STYLE # 50344
Available colors

  • Leather lace-up chukka shoes
  • Durable cowhide, padded ankle, removable comfort insole, high-traction rubber sole
  • 1.20" heel, 3.70" shaft, 1.25 pounds


Overland’s chukka style shoes are a natural for everyday wear, thanks to the sturdy design in smooth cowhide leather with lace up support, reinforced ankle collar, a removable orthotic insole for all-day ease, and the trusted traction of a comfort box sole.
1.20" heel, 3.70" shaft, 1.25 pounds
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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

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 4 customers
4 of 4 reviews
Yesmam from TX (Texas)
Jan 1, 2020

Very comfortable

5 5
Was loking for something not to formal, yet able to wear for going out for nice rustic Steak and Wine dinner
Pat from New Jersey
Nov 23, 2019

Great quality shoes

5 5
Very comfortable and the quality is excellent. Exactly what I was looking for.
G.C. from Chicago Illinois
Oct 11, 2018


5 5
Wear them almost every the look and feel.but they run a little wide.
Peter from Spokane, WA
Oct 6, 2018

Well built shoe

4 5
These shoes are a classic look with a firm thick sole and a wide toe box, exactly what I need when I'm on my feet all day. I initially had some friction behind my heels and for that reason cannot give 5 stars. I'm very happy with this purchase.

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Our Values

A lot has changed since our humble beginnings in Taos, NM, 50 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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