The Uptown Chestnut

Effortlessly stylish and built for those who demand both sophistication and rugged durability, The Uptown Chestnut is the perfect fusion of classic Western heritage and modern refinement.

Crafted from premium chestnut brown leather, this boot boasts a slightly distressed finish that speaks to its character—rich, worn-in, and effortlessly cool. The pointed toe and sleek silhouette offer a refined edge, while the unique side-zip closure adds both convenience and a contemporary touch.

Designed for Comfort & Longevity

• Full-grain leather construction ensures a supple yet durable feel that only gets better with time.
• Goodyear welt craftsmanship for superior durability and the ability to be resoled.
• Leather insole & soft lining provide all-day comfort, molding to your foot for a personalized fit.
• Low-profile heel & flexible outsole offer a smooth ride whether you’re strolling city streets or stepping into a high-end venue.

A Statement of Effortless Versatility

Whether you're pairing them with tailored denim, a crisp button-up, or a well-cut suit, The Uptown Chestnut exudes confidence and class. Equally at home on the pavement of a metropolitan night or in the relaxed setting of a country escape, this boot is made for those who appreciate the finer details.

Proudly designed by Square To Toe®, The Uptown Chestnut isn’t just a boot—it’s a mark of refined taste and timeless quality.