All day lightweight comfort

Chicago Travel Plain-Toe Derby


Item# SF2911
$345.00 $179.97


  • Select Color 2911 Black

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Additional Information



  • Lightweight, comfortable dress shoe designed for the business traveler
  • Non-stop comfort for all day wear
  • Dress it up or down, perfect any way you style it
  • Classic Fit, fits true to size


  • 360º Feather Welt for lightweight shock-absorption
  • Removable Traveler cushioned insole
  • BounceX cork and foam midlayer creates a custom fit
  • Lightweight blown rubber sole
  • Craft

  • Built on the welted 511G Last
  • Premium calfskin leather upper
  • Recraftable
  • Imported
  • 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
    Chicago Travel Plain-Toe Derby is rated 2.8 out of 5 by 6.
    Rated 5 out of 5 by from Excellent travel shoe Comfy and smart with rubber sole. Good for airports and evening
    Date published: 2020-02-04
    Rated 3 out of 5 by from Quality AE Quality of their product has been declining over the past several years. I have been a customer for 30+ years and I will be looking for a different brand next time.
    Date published: 2021-06-28
    Rated 3 out of 5 by from Short heel The shoe seems well made but the fit is what I would describe as sleek. The heel is low and the D is a narrow D. I returned for a Park ave in a width wider and it’s much better. I don’t think a width wider in this shoe would have solved the low heel issue. It just didn’t grip my heel with each step. If you have a narrow foot and don’t mind a low heel this might be your shoe.
    Date published: 2021-04-16
    Rated 3 out of 5 by from Nice cushioned sole, weird fit. I bought these in an 8D which is what I wear in several other shoe brands and I found they run quite wide. They also have a tall cushioned insole and low heel resulting in the shoe sitting low on the foot and my heel almost slips out. Unfortunately I realized this while wearing them on a work trip otherwise I probably would have returned them. Besides the fit issue they seem well made. Mine came with a tiny scuff on the leather but no serious imperfections. The leather upper and liner are soft and supple. Just as you would expect for a travel shoe the sole is very comfortable for walking. It feels almost like a hiking boot sole. My old shoes hurt my feet and these totally fixed that problem. They also go through metal detectors fine.
    Date published: 2020-08-24
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    Is it goodyear construction?

    Hi, It seems from the pictures, specifically the picture of the sole from below, that it is a cemented sole, or at least the last layer. Is that right?
    Asked by: AbdoQ
    Thank you for your inquiry regarding the Chicago Travel Plain-Toe Derby! This style has a 360º Feather Welt for lightweight shock-absorption which is a type of Goodyear welt. We hope this information helps!
    Answered by: CUSTOMER SERVICE
    Date published: 2021-04-26

    Are these more suited for boys of adults?

    Asked by: Namal
    Allen Edmonds does not offer kids or youth shoe sizing, all shoes are marked with Mens US sizes. Thank you for your question!
    Answered by: CUSTOMER SERVICE
    Date published: 2020-05-06

    Are these shoes airport friendly, no shank?

    Are these shoes airport friendly, no shank?
    Asked by: TJ
    The Travel Collection, including the Chicago style, are airport friendly and do not have metal shanks. Keep in mind, as airport security expands their screening technology and restrictions shoe removal may still be mandatory at security checkpoints for most individuals. If you have other questions, feel free to contact us again!
    Answered by: CUSTOMER SERVICE
    Date published: 2020-04-20

    1) what type soles may be selected with this shoe? 2) do you ever sell a pair of shoes with each shoe a different size?

    I must wear a brace on none foot.
    Asked by: Steven
    The Chicago Travel Plain-Toe Derby is not currently available for customization. In addition, we do not currently offer mismated orders.
    Answered by: Customer Service
    Date published: 2020-04-14
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