This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.


Cart 0

No more products available for purchase

Add order notes
Pair with
Congratulations! Your order qualifies for free shipping You are $250 away from free shipping.
Subtotal Free
View cart
Shipping, taxes, and discount codes are calculated at checkout

Josephine Chelsea Boot Dark Oak Roughout


The Chelsea boot is steeped in both fashion and practicality. Originating in the mid-19th century in England, the first Chelsea boot was explicitly made for Queen Victoria. Her personal bootmaker, Joseph Sparkes Hall, created the first Chelsea boot – originally called Elastic Ankle Boots – in 1851 as a riding boot for the Queen. Yet, it took over a century for the Chelsea boot to arrive in the States. Becoming particularly fashionable during the swinging '60s in London, specifically in the Chelsea district of London, the Beatles brought their regal boots to the American masses.

The Josephine Chelsea boot – named after its inventor – remains essentially the same as it did for the Queen. Featuring elastic side panels and a sleek, ankle-high design, the Josephine Chelsea boot is perfect for those on the run, offering both style and convenience. A truly timeless, elegant, and versatile boot you will want to wear every day, whether you're strolling down city streets or striding into work. 

  • Goodyear-welt construction
  • Victoria last
  • Oiled/Waxed Roughout from Charles F. Stead 
  • Full-grain leather cow lining
  • Double-sided gore
  • 360º flat welt
  • Vegetable-tanned leather insole, welt, and midsole
  • Cork filler with steel shank 
  • Full-grain leather heel counters
  • Micro stud outsole for year-round wear

Every pair crafted on Xiamen Island, China

Our women's footwear runs true-to-size. Our customers typically take our women's styles in their average boot or sneakers size. 

Not sure? Send an email to referencing your current sizing for help.

Enjoy fast, free shipping on orders over $250 in the contiguous US. Orders are processed and shipped within 1-3 business days.

Contiguous U.S. Returns:

  • Free exchanges
  • Refunds - A $15 restocking fee per pair is held when using the prepaid label

For more information, please visit our Help Desk.

Free 15 Days Exchange on Domestic Orders

[{"variant_id":"40200620146774" , "metafield_value":""},{"variant_id":"40200620179542" , "metafield_value":""},{"variant_id":"40200620212310" , "metafield_value":""},{"variant_id":"40200620245078" , "metafield_value":""},{"variant_id":"40200620277846" , "metafield_value":""},{"variant_id":"40200620310614" , "metafield_value":""},{"variant_id":"40200620343382" , "metafield_value":""},{"variant_id":"40200620376150" , "metafield_value":""},{"variant_id":"40200620408918" , "metafield_value":""},{"variant_id":"40200620441686" , "metafield_value":""},{"variant_id":"40200620474454" , "metafield_value":""},{"variant_id":"40200620507222" , "metafield_value":""},{"variant_id":"40200620539990" , "metafield_value":""}]

Josephine Chelsea Boot Dark Oak Roughout


Made with

Goodyear-welt Construction

Renowned for its durability and ability to be resoled repeatedly, Goodyear-welt construction involves stitching a welt—a strip of leather or rubber—around the shoe's perimeter, creating a cavity. After filling the cavity with the shank and cork, the sole is attached, providing strength and water resistance. This construction method results in shoes that are not only long-lasting but also easily repairable, making them a timeless investment in quality craftsmanship.

Our mission

Providing Excellent Service

Our priority has been putting customers in shoes that properly fit them and standing by our amazing products. Many customers have found they have been wearing an incorrect size for years. This has been lost in the market today. We offer the majority of our footwear in D, E, and EEE widths to provide well-fitting footwear.

We encourage customers to ask our team for assistance to ensure the best fit.