Limited Edition, Made in USA

Cap-Toe Trench Boot

Cognac Shackleton
$428.80 Regular Price $536.00

True-to-Size: For an ideal fit, we suggest selecting your "true" size as measured on the Brannock Device or your typical size in dress shoes or other fine footwear. You should expect a somewhat snug fit that will become more personalized with regular wear as the leather stretches and conforms to your foot.

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Trench Boot

Trench Boot Cap-Toe Leather Sole Technical Drawing

Hand-lasted 360° Goodyear Welt Construction. Horween® Shackleton® Leather. Partially-Structured Plain Cap Toe. Black Dainite® Rubber-Studded Sole. Stacked Leather Heel with Dainite® Toplift. Barbour® Welt with Hand-Brushed Edge Sealant. Calfskin Vamp Lining. Tone-on-Tone Stitching. Polished Brass Eyelets & Speedhooks. Flat Waxed Cotton Laces.

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Elston Last

Oak Street Bootmakers Elston Last Technical Drawing

Developed to embody the character of Chicago, the Elston last is engineered specifically for our line of Everyday Boots, providing exceptional all-day comfort for nearly all foot types with a generous toe box.

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Dainite® Studded Sole

Dainite Rubber Studded Sole Technical Drawing

Dainite's rubber-studded soles are as practical today as they were when introduced in 1894. Since then, Dainite continues to make its famously durable soles in Leicestershire, England. Reinforced with Silica and Aluminum silicate, these non-marking soles are highly regarded for all-weather traction and timeless style.

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Horween® Shackleton™

Horween Tannery Logo

Named for polar explorer Sir Ernest Shackleton, Horween's latest tannage adds an all-new formulation of fat liquors to one of the family's oldest leather recipes. The result is a waterproof leather with extremely heavy pull-up, a hand as supple as a well-loved baseball glove, and a buttery-smooth finish. While the patination and elasticity may remind one of Horween's own Chromexcel, Shackleton's dramatic high and low tones, creamy tactility, and glassy-smooth surface speak to the uniquely-refined character of leather worthy of the name Horween.

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More than Made in USA

United States of America Flag

We are 100% committed to manufacturing all our footwear and accessories in the United States.

Fully Recraftable

Oak Street Bootmakers Recrafting Services Icon

All our footwear is 100% recraftable, meaning it can be re-soled again and again.

Horween Shackleton Leather

Over a Century of Exploration

The Horween Leather Company was founded in 1905 during the “Heroic Age of Antarctic Exploration.” In 1911, while Sir Ernest Shackleton was developing plans for his “Imperial Trans-Antarctic Expedition” from South America to Australia—by way of Antarctica—Isidor Horween was developing a water-resistant leather he would soon bring to market as Chromexcel. Over a century and four Horween generations later, Isidor’s journey has reached a new milestone with Shackleton: a distinctive waterproof leather as well-suited for the perils of maritime exploration as it is for pipes with the Fellows of the Royal Scottish Geographical Society.