Handcrafted in the USA, with fine imported materials

Williamsburg Chukka Boot


Item# SF2799
$445.00 $199.97


  • Select Color 2799 Black

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Additional Information



  • Clean, classic dress chukka boot
  • Two-eyelet plain-toe boot
  • Dress it up or down, perfect any way you style it
  • Classic Fit, fits true to size


  • 360º Bench Welt construction for durability and stability
  • CustomCork™ insole forms a custom fit
  • Single oak leather sole
  • Craft

  • Handcrafted in Port Washington, WI, with fine imported leathers
  • Built on the 65 Last
  • Premium European calfskin leather
  • Soft tan leather lining
  • Recraftable
  • Care

    We believe a great pair of shoes or boots is always a solid long-term investment. To keep your favorite footwear in top form for years or even decades to comes, use our 4 Step Shoe Care Process and these essential products.

    1. Clean

    Start by applying Saddle Soap with a Cotton Flannel Polishing Cloth to remove stains and dirt from the uppers and bring up the leather's natural oils.

    2. Polish

    Next, use a Horsehair Dauber to treat your footwear with Cream Polish which renews the color and luster of leather. Any time you want to achieve a truly glossy, high shine, you should instead apply Carnauba Wax Polish.

    3. Dress

    Restore the color and surface of the leather on the heels and soles using Heel Dressing.

    4. Protect

    Leather Lotion keeps uppers soft, supple and hydrated while a Horsehair Shine Brush is perfect for buffing your shoes to the desired shine. As a last step, spray on Water Protector to guard against harmful moisture and spills and use a Leather Dopp Kit to keep all your care products organized.

    Looking for replacement laces? Find the right laces for your Allen Edmonds shoes and boots here: Shoelace Fit Chart


    Classic Fit

    Most people consider a “classic” fit to be a “standard” fit. This fit more closely aligns with the natural shape of your feet.

    U.S. E.U. U.K.
    5 38 4
    5.5 38.5 4.5
    6 39 5.5
    6.5 39.5 6
    7 40 6.5
    7.5 41 7
    8 41.5 7.5
    8.5 42 8
    9 43 8.5
    9.5 43.5 9
    10 44 9.5
    10.5 44.5 10
    11 45 10.5
    11.5 45.5 11
    12 46 11.5
    12.5 47 12
    13 48 12.5
    14 49 13
    15 50 14
    16 50.5 15

    For help getting the perfect fit, we recommend you visit a retail store to get your feet fitted. If you do not have the option to visit one of our stores, you may contact customer service to help you choose the right size.

    Width Available Sizes
    AAAA 8.5-16 Narrow
    AAA 10-12, 13, 14
    AA 10-12, 13, 14
    A 9-12, 13, 14
    B 8-12, 13, 14, 15
    C 8-12, 13, 14, 15
    D 6-13, 14, 15, 16 Medium
    E 6-12, 13, 14
    EE 6-12, 13
    EEE 7-12, 13, 14 Wide


    We believe making a great pair of shoes or boots is a long-term commitment. That’s why we construct our styles with handcrafted bench welts, ensuring our experts can rebuild your footwear and you can count on years of exceptional wear.

    Our recrafting service saves over 70,000 pairs of shoes from landfills each year.

    From refinishing the uppers to replacing the soles, we offer a full range of packages for extending the lifespan of our timeless designs.

    Ask & Answer
    Williamsburg Chukka Boot is rated 4.3 out of 5 by 18.
    Rated 5 out of 5 by from Beautiful, high-quality boots I have many pairs of Allen Edmonds shoes and boots and these are my favorite pair. They are extremely comfortable, and work with just about any clothes I wear. They are true to size. I wear a 11.5 Wide (EEE) and these fit perfectly. The craftsmanship is superb.
    Date published: 2021-06-11
    Rated 5 out of 5 by from My first pair of Allen Edmonds. Couldn't be happier. Two years ago, I made a personal choice to look "Made in USA" first with EVERY purchase I made. It has been a daunting task. My shoe size as measured by an Allen Edmonds associate, (thanks Brian) is a 10EEE. Needless to say, wide widths are difficult to find. During my web searches for a "made in america" wide shoes and boots, I came across Allen Edmonds on line. I visited the site and then found there was a store only 40 minutes from my northeast Ohio residence. There, I was greeted by Brian, an AE associate. He measured my feet, as I knew they did differ in size and then spent an enormous amount of time with me trying on different boots with different sizes. Ultimately I went with the Walnut Williamsburg Chukka in 10EEE. They didn't have my color so he ordered it and sent it directly to my home. Fortunately, I caught a sale on this particular boot which made it even more a win-win. Now to the boot came in a wonderfully designed box. I'm the guy that wipes them down and puts them in the original box after each wearing. In the heavy duty box was the boots with a beautiful fleece drawstring AE shoe bag. I LOVED it!! Well done AE. The boot color was the same but slightly different subtle variations from boot to boot. THIS IS NORMAL with finished leather folks. If you want perfect color, then get them in black!! 360 deg welt allows for recrafting, which means they can be re-soled. They fit wonderfully. They were comfortable. I did wish there was 1 more set of lace holes to come up a little higher on the vamp.The waxed laces were a bit thin for my liking and were hard to tie with my fat fingers. Also, they came loose very easily while walking in them. I pulled them out and threw them away and replaced them with a slightly larger gauge and longer waxed lace. Made all the difference.I tuck the lace loops and ends into the side of the boot for a cleaner look so I got them longer to get better leverage for a tight tie. I immediately treated the leather sole with a leather conditioner and preservative as it was winter here and I find the salted sidewalks can dry out leather rather quickly. Inside leather is smooth and even with a thin sock there is no binding. Cork sole is already starting to conform to my feet. Gotta say, I will most likely get another pair in black to go with some darker jackets and sweaters, but I do love these and you will too. Visit a store and talk with an AE professional. If you do go get them on line, get both your feet measured and get your size and width. IMO they run "true to size". Hope this helps. Good luck!
    Date published: 2020-02-20
    Rated 5 out of 5 by from Comfortable perfect fit Excellent construction, smooth supple leather for comfortable fit.
    Date published: 2020-02-12
    Rated 5 out of 5 by from Very attractive dress boot I have two pair of these boots (dark brown and black). They go well with nicer slacks and dress trousers. I believe quality ankle length dress boots give a nice line to properly fitted trousers and slacks.
    Date published: 2020-02-08
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    When is their more sizes in stock?

    Asked by: Mo93
    We're sorry, the Williamsburg style is discontinued and there are currently no plans to restock it. If you have other questions, feel free to contact us again.
    Answered by: CUSTOMER SERVICE
    Date published: 2021-05-16

    If I wear a size 9d in a Chelsea Lombard boot what size would I wear in the chukka boot?

    I went into an Allen Edmonds store today and was measured for the Chelsea Lombard Boot and was told I would wear a size 9 D in that boot but since it's not on sale anymore I've decided to go with the chukka boot. What size would I wear in the chukka boot if I wear a 9d in the Lombard boot and how long is the sale going to be lasting on the chukka boot? What is the last on the chukka boot? I know in the Lombard boot it's a 64 last. Do the Chukka Boots offer room in the width part of the foot and are they comfortable to walk in and do they have enough room for my orthotics if I need them? I have numb feet and trouble with balance are these good boots for a person in my situation? Also when I go on your website I'm told by the website that the true fit size I wear is a 10d which doesn't go along with what the salesman at the Allen Edmonds store told me today which is that I wear a 9d Who do I believe? The tru fit or the salesman? Thanks for your response, David Henry
    Asked by: Apollo
    Stay with the 9 true fitting you had at the store, consider a little more width like an E, down the road if those conditions result to occur then consider a EEE. Hope this was helpful.
    Answered by: cadmike39
    Date published: 2021-02-13

    What kind of brown is the coffee color?

    Is it more of a medium or dark brown?
    Asked by: Egi26
    It is a dark brown color.
    Answered by: Anonymous
    Date published: 2020-12-12

    May I return the shoes if the size does not fit and the shoes ar unmarked?

    I have a bunion on the right foot should I order a size E rather than a size D?
    Asked by: Anonymous
    You can return this item as long as it unworn. We recommend trying the shoes on a carpeted surface. Also, we would recommend purchasing the size you normally wear in dress shoes and base the fit by how you feel inside of the shoes.
    Answered by: Anonymous
    Date published: 2020-11-24

    Can I order the Williamsburg Chukka boot, black 12 EEE with leather sole?

    Asked by: crazyeddie101
    This style is currently available to order online in your preferred size. If you need assistance placing an order, please call 877-817-7615. Thank you!
    Answered by: CUSTOMER SERVICE
    Date published: 2020-04-23

    What is the drop between the heal and the toe?

    What is the drop measurement between the heal and the toe? Am I able to order modest variations to the drop/heal stack such as +/- a few millimeters or a different material such as cork instead of leather?
    Asked by: William
    The heel drop to the sole is approx. 15mm.
    Answered by: mheidenr
    Date published: 2020-02-20

    Can it be ordered in cordovan leather Chukka boot

    Asked by: Thomas
    Hello, Thank you for your inquiry! Unfortunately, we not offer the Willamsburg in cordovan. -AE Consumer Care Dept.
    Answered by: Anonymous
    Date published: 2019-11-06

    may i order these with the Dainite sole

    Asked by: Joe
    Absolutely yes!
    Answered by: dng
    Date published: 2020-02-12

    What accessories go with shoes, looking for a belt.

    Asked by: Anonymous
    Thank you for your inquiry regarding a belt to go with the Williamsburg Chukka boots! This really depends on what color your boots are. You can check out our current line of belts via this link: https://www.allenedmonds.com/accessories/belts/ We hope you can find one that works perfectly!
    Answered by: Customer Service
    Date published: 2019-09-02

    Do you still have dress boots made of boar skin?

    Asked by: JayJay
    Thank you for your inquiry! The Williamsburg Chukka boots are made of calfskin leather. We also don't currently have any other styles made of boar skin. We hope you can still shop with us!
    Answered by: Customer Service
    Date published: 2019-09-02
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