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

    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
    Chicago Travel Plain-Toe Derby is rated 3.3 out of 5 by 3.
    Rated 2 out of 5 by from I'm sad I had to return my purchase. Unfortunately, the quality control wasn't good. Likely it was 2nd. I returned it because on one shoe the toe support reflected through the leather, it revealed like a seam. Otherwise, l like the shoe style.
    Date published: 2021-01-14
    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
    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
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    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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