Handcrafted in the USA, with fine imported materials

Williamsburg Chukka Boot


Item# SF2799
$445.00 $345.00


  • Select Color 2809 Walnut

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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 naturally molds for 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

    Care Instructions

    STEP 1: Using a damp cloth or sponge, lather our Saddle Soap and apply onto leather to clean and restore its natural oils.

    STEP 2: Moisturize the shoes with our Cream Polish to make them supple and soft, following instructions on the product.

    STEP 3: Condition the shoes with our Speed Polish, protecting them from dirt, rain and snow.

    STEP 4: Take our Heel dressing applicator and apply to the edge of the heel and sole.

    STEP 5: Apply our Leather Lotion as needed for added protection and polish in between cleanings. Use our Horsehair Shine Brush to buff shoes to a desired shine.

    *For camo printed leather, simply rub our Leather Lotion onto print with our Cotton Flannel Polishing Cloth as needed and wipe smudges or dirt away with a damp cloth.

    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
    Ask & Answer
    Williamsburg Chukka Boot is rated 4.5 out of 5 by 8.
    Rated 5 out of 5 by from Love these boots! That's all I have to say! You'll love them too! Order them now!
    Date published: 2019-12-05
    Rated 5 out of 5 by from Well-made, Dressy Shoe that happens to be a Slim, Stylish Boot This is my second pair of Allen Edmonds chukka style boots and I'm extremely pleased with this purchase. The fit and finish of the boots is superb, on par with any dress shoe made by AE or other American crafted dress shoe makers. The style leans more formal, similar to that of a whole-cut dress shoe with a very low-profile sole. If one didn't know that it was a chukka, you'd swear it was a plain-toe whole cut. There are one or two things that could be improved. I agree with other reviewers that the laces seem short, they are "just" long enough for a single knot. I replaced them with longer waxed laces for my double-knot comfort, $5 well spent. An additional laces hole is a mixed bag, might be an improvement, but then might not as sleek of a look. This could be my favorite shoe purchase ever. Only more walks, dinners and meetings will tell. Allen Edmonds is back in great form.
    Date published: 2019-11-19
    Rated 3 out of 5 by from Fantastic boot but too narrow for me. Beautifully made great looking boot but even at 3E it was too narrow for me. I have a high instep so the top of the boot didn't come close enough when tied to look good. Unfortunately I had to return the boots but will try again.
    Date published: 2019-11-14
    Rated 4 out of 5 by from Comfy-Casual with Allen Edmonds Pizazz A comfortable shoe, right outta the box. Which is more than you can say for a lot of boots. Because of the relatively low rise, ankle-height of the upper, you never have that “I’m wearing ski boots” feel when they are new. Conversely, the minimal eyelets take a bit of getting used to, as it seems like there is not enough shoelace there to keep everything in place (there is). Swankier than a AE’s plain-toe derby or blucher, Chukkas go well with khakis, jeans, etc. Though some say they’re good with sport coat attire or even suit...nah. There are other shoes for that. These are pretty casual. For those fleshing out their wardrobe, I’d consider these a second-level purchase — to buy once you already have dress boots, casual boots, dress shoes (in cordovan, black, and brown and/or chestnut), and leather sneakers. (Btw, I bought leather sneakers in another brand; sorry AE.) So if you go to casual BBQ or social meetups, this Chukka meets the bill; and suggests you might be doing well enough to own more than 3 pairs of shoes. And perhaps you are.
    Date published: 2019-11-14
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    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

    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
    I'm not sure if you can order these with Dainite. The standard leather sole is very low-profile and might change the look of the boot, if you don't mind that.
    Answered by: PolitiTech_Consultant
    Date published: 2019-11-19

    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

    Can you please provide the black Danite option on this sole? It has the same last as Strand which has black option. Thanks!

    Asked by: Anonymous
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