Handcrafted in the USA, with fine imported materials

Williamsburg Chukka Boot


Item# 2809-105-B
$445.00 $249.97


  • Select Color 2809 Walnut

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In Stock: Ships in 3-7 business days

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

    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 4.0 out of 5 by 1.
    Rated 4 out of 5 by from Classy yet casual I have been wearing Italian Blake Stitched shoes as i am born and raised Southern California but recently moved to Washington state and Blake stitch is not the best stitched shoe for 5 months of rain. Found these AE chukkas with a really nice style and on sale for $299, after reading many Reviews and watching many YouTube videos on AE I thought this was a great buy and they are a great buy! A couple things I will add, they are not the color as shown on the website with a nice caramel color, they come very cool tan kind of drab without the darker caramel color at the toe like on the website. The laces are very thin for a chukka but I find I like them. The eyelets are set a bit lower than other chukkas and kind of feel like they are untied when walking around but I really like it because the break in period is shorter since the ankle leather is not tight against your lower leg with the lower eyelets you feel a little free walking as if you are wearing shoes not chukkas. I took the advice of many YouTubers and shined them out of the box and since I really liked the caramel color on the website I bravely added a reddish wax, then neutral, then brown (yes brown) to the toe and lower sides of the front to give it the caramel color I was expecting and I love them. The inner soft leather and shoe insole are very comfortable. I don’t feel the cork softness in the sole many brag about with Goodyear welting compared to Blake stitch but they are as comfortable as my Italian Blake stitched shoes. Overall I’m very happy with this purchase and I may buy the chili color if they ever go on sale ha ha. Only reason why I rated this four stars is because I did not like the pale drab cool color they came in not the nice warm caramel color shown on the website. I do recommend the shoes for anybody who would like a comfortable classy looking chukka to dress up or dress down with denim. I wish I could add pictures to show you the colors.
    Date published: 2020-05-26
    • y_2021, m_3, d_5, h_16
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    • clientName_allenedmonds

    why is this not offered in a 7 or 6.5?

    Why is this not offered in a 6.5 or even a 7.??
    Asked by: Carey
    The Williamsburg boot is a closeout style and we will not receive any new inventory. The sizes that are on our site is what we have available. Unfortunately, we are sold out of sizes 7 and 6.5.
    Answered by: Anonymous
    Date published: 2020-10-12
    • y_2021, m_3, d_5, h_16CST
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    • clientName_allenedmonds

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