SKU: 59941671620

Eastwood Chelsea Boot R Chestnut

Sale price$158.40 Regular price$176.00
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Description

Eastwood Chelsea Boot R Chestnut"I get compliments all the time" The Eastwood look is classic and clean, comfortable on and with a timeless style. Chelsea boots are quite versatile they can be worn with smart clothes or casual with jeans. Chestnut goes well with most colours and in particular blue. The stitched leather sole includes a rugged commando style rubber overlay to make them better in the wet and makes them last even longer before needing resoling. Photo: @ilhamigozcu

"I get compliments all the time"

The Eastwood look is classic and clean, comfortable on and with a timeless style. Chelsea boots are quite versatile - they can be worn with smart clothes or casual with jeans. Chestnut goes well with most colours and in particular blue.

The stitched leather sole includes a rugged commando style rubber overlay to make them better in the wet and makes them last even longer before needing resoling.

Photo: @ilhamigozcu styles them with blue jeans.

  • High quality full grain calf leather
  • Hand dyed chestnut patina
  • Burnished toe
  • Full calf leather lining
  • Blake stitched sole with rubber commando overlay
  • Includes dust bags
  • Made in Italy


Chelsea boots were originally invented in England as riding boots before becoming world famous in the 1960s, worn by the Beatles and getting their name from the fashionable Kings Road in Chelsea . Eastwood is an ankle boot as compared with our Fleetwood Chelsea which is a mid calf boot. Read more about chelsea boots for men in our chelsea boot style guide.


Hand finished chestnut patina

This Eastwood chelsea boot is in a very nice, hand finished oxblood patina. Oxblood looks fantastic with blue or black jeans, also chinos, and even a suit. We also have them in other colours, including oxblood, brown, blue and black, also suede including grey and tan. The colour is very rich and deep. It has been built up in layers and then waxed and polished to protect and enhance the finish.

Full grain calf leather

They are hand crafted in Italy, using the finest, full grain calf leather. They have an elegant, clean, sophisticated pattern, very nice lines. It's a beautiful piece of leather. The toe is slightly longer than some other brands, which is typically Italian, and is nicely rounded. For many the convenience of chelsea boots is that there are no laces. They're the boot version of a step in loafer. There is an attractive sweeping line from the toe to the ankle We achieve this with our special blocking process, a very skilful process, using a roller to smooth and shape the leather. The result is a clean, sweeping line with no creases.

Craftsmanship/attention to detail

There is a twin elastic gusset, with a nice shape, not square or rectangular. We use a high quality elastic which should keep its elasticity for many years. There is a leather strip from the heel all the way up. It incorporates a strong nylon pull loop, that adds strength, which is important when you pull the boots on. The shaft height which is from the top of the heel to the top of the boot is about 15cm or 6 inches. So if you are sitting, your socks won't normally be visible. The boots provide excellent support around the ankle. It's important to have a carefully shaped last. We based this design on a lot of testing and feedback - so it's generally seen as a very great fitting boot.

There is a nicely rounded top line, with no raw edges, as we taper or ‘skyve’ the edge, then fold the leather and stitch it. Looking inside, we see the Thomas Bird branding, embossed into a piece of calf leather, foam backed for added comfort. The boot has a full calf leather lining. This helps absorb moisture and prolong the life of the boot. And we use a genuine full leather insole. Inside the heel, we use suede to stop your heel slipping. What you can’t see are the stiffeners between the calf upper and lining. There is one in the toe and another at the back, around the heel. These are important to keep the shoe looking good as it ages, and we use longer, high quality stiffeners to achieve this.

Stitched leather sole

The sole is stitched onto the upper with a traditional Italian method called blake stitching. This is an in-channel, lock stitching technique, so even if one stitch was worn the others will still be locked securely in place. And being stitched the sole can be replaced when it eventually wears. But to extend the sole’s life, we use a rubber insert for added wear and better grip.

Stacked leather heel

There is a 25mm genuine leather stacked, heel, with 4 brass pins, and a rubber piece, again for better wear and grip, that can be easily replaced. Our Eastwood oxblood chelsea boot has a classic cut with an elegant line. It's a beautifully Italian made high quality boot, that with care should give you many years of enjoyment.

    Shipping Notes
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    Exchange/Return Notes
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    SKU: 59941671620

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    Based on 1617 reviews
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    Skribbles76
    Bozeman, US
    ★★★★★ 4
    Comfy and cute.
    I was looking for a Converse alternative for a multitude of reasons. These were perfect. I love the slip-on style. The leather laces stay in place much better than the Converse cotton laces and there is way more sole support, which is a huge plus. I purchased these in black about a year ago and then went for the camo pair. As for the black pair, I wore them regularly for a year. After that time, the shoe didn't feel as comfortable anymore, and the fabric outer around the ankle began to fray, and the white outer trim was beginning to detach from the bottom sole. With that, I was pleased with how long they lasted. As for the camo pair, I anticipate the same quality and comfort. While super cute, the only draw back is the mismatched pattern. If you look at the pics, the one shoe has more gold embellishment at the toe area and the other one doesn't. This bothers me a bit as I would have liked it to match. Otherwise, I'm happy with both purchases so far and will continue to buy them in the future.
    WAS THIS REVIEW HELPFUL?YesReportShare
    Reviewed in the United States on June 27, 2023
    D
    Verified Purchase
    Doris Stanley
    Charlottesville, US
    ★★★★★ 5
    Love these
    Size: 7, Color: Camo Olive
    Love these shoes. Great value and comfortable
    WAS THIS REVIEW HELPFUL?YesReportShare
    Reviewed in the United States on May 2, 2026
    T
    Verified Purchase
    Texas 12
    Port Orchard, US
    ★★★★★ 5
    Long lasting. Sperry is quality.
    Last a long time and still look good.
    WAS THIS REVIEW HELPFUL?YesReportShare
    Reviewed in the United States on January 20, 2026
    B
    Verified Purchase
    Bea
    Omaha, US
    ★★★★★ 5
    Best buy
    I love these it's been a while since I bought them and still look like brand new.
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    Reviewed in the United States on February 12, 2026
    J
    Verified Purchase
    Jessica
    Phoenix, US
    ★★★★★ 3
    Cute but no so comfortable
    I previously owned a white sperry leather shoe that I bought from Marshall’s for about $35 & absolutely them, they were so comfortable , cute & great price.After running that pair down, I decided to buy another pair and found out the shoe was discontinued. The closest thing to what I had is this, the white crest vibe in leather. I was disappointed that this shoe was not as comfortable and didn’t fit quite the same. The back ankle part of the shoe caved into my skin and hurt. Sadly, I do not recommend this shoe for much walking. I hope Sperry decides to make this shoe more comfortable because it is cute.
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    Reviewed in the United States on September 25, 2021

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