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Josephine Chelsea Boot Dark Oak Roughout

$296.00 Regular price $395.00
Size5.5

Free Exchange on Domestic Orders

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 in our factory on Xiamen Island, China

Our Luna- and Victoria-lasted 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 info@grantstoneboot.com referencing your current sizing for help.

Enjoy fast, free shipping on orders over $300 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.

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Josephine Chelsea Boot Dark Oak Roughout

$296.00 Regular price $395.00

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—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.

Overall rating: 4.9 / 5 from 10 reviews.

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Reviews

Beautiful Chelsea Boots!

"My Josephine Chelsea Boot in Dark Oak Roughout is beautiful and performs well in any weather! I couldn’t be any happier! Looks great with jeans, dress pants, literally anything. Thank you Grant Stone for a great product!"

Kristin S. (5/5)

Top Quality Boots! Standout Leather! Excellent exchange process.

"I bought these for my son’s girlfriend as a Christmas present during the Black Friday sale. As always, the Grant Stone boots quality and craftsmanship are top-tier. The Dark Oak Roughout Leather is incredible which will develop multiple color variations and textures over time. Sizing: We initially followed the "true to size" Fit Guide recommendation, but they were much too large. We ended up going a full size down (from 7. 5 to 6. 5) for the perfect fit. The Exchange: I was particularly impressed with the “Return Gift” process. Since the recipient lives in a different location, this allowed her to handle the exchange directly without me having to play middleman. The turnaround was less than a week, getting the right size to her just in time for Christmas. So what does she think about the boots? Her quote says it all: “I’ve never felt cooler in a pair of boots!”"

James H. (5/5)

Great boots, comfortable and look great

"These boots look exactly as shown on the website. Sizing guidance was helpful. With a few wears to date, they feel comfortable and I’m very happy with them"

Kamala R. (5/5)

Beautiful Boots! Superb Quality!

"I am absolutely in love with these boots. The quality is superb and the comfort out of box impressive. As a woman with size 12 feet, I have struggled to find good looking, quality women’s shoes. I am so happy to have found Grant Stone—I’ll definitely be adding another pair in the future!"

Sara B. (5/5)

What is my wife as

"What is my wife as a special gift and she absolutely loves them. Same quality I've come to expect from the men's 's shoes and boots"

Phillip F. (5/5)

"Got them for my wife. She thought they were a little stiff at first, absolutely loves them after her second day breaking them in."

Charlie (5/5)

"My wife loves these boots. They look amazing on her."

John (5/5)

"It’s very difficult to find high-quality, Goodyear-welted footwear for women and this is an outstanding product equal to the quality of their men’s footwear line — highly recommended."

William (5/5)

Grant Stone Quality

"Fit well and with typical Grant Stone quality"

Nelson G. (5/5)

Splendid boot but wrong size.

"Very good boot I must say but it's a shame it was the didn't fit me so had to return them."

Aminh N. (4/5)

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