$25 restocking fee on returns

Factory 2nd - Wooster Street Penny Loafer


Item# SF2288S
$395.00 $149.97


  • Select Color 2289S Cigar

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Additional Information



  • Modern, yet classic slip-on penny loafer
  • Dress it up or down, perfect any way you style it
  • Relaxed Fit, slightly roomy feel


  • 360º Speed Welt for enhanced flexibility and shock absorption
  • Comfortable ShockForm™ insole cushion
  • BounceX foam and cork midlayer
  • Lightweight heel
  • Quarter heel tap and non-skid rubber pod for traction
  • Craft

  • Handcrafted in Port Washington, WI, with fine imported leathers
  • Built on the 64 Last
  • Premium European leather
  • Premium leather lined
  • 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


    Relaxed Fit

    The relaxed fit has added space in the toe box. This extra room allows for thicker socks and foot expansion that occurs at the end of the day or during a long flight.

    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

    Is chili color similar to oxblood?

    Asked by: Sunny
    Chili is a warm color, or reddish-brown, while Oxblood is a cool color, more burgundy. Thank you for your question!
    Answered by: CUSTOMER SERVICE
    Date published: 2021-05-21

    Do you sale Carbon shoe polish? If not ,what is a good shoe polish color to use?

    Asked by: William
    We recommend Neutral polish for this style, as this is what is used at our factory during finishing. We do not sell Carbon shoe polish. If you are unable to cover any deep scuffs, you can spot treat them with a small amount of a dark shoe polish such as black to minimize their appearance. We do recommend trying it on an inconspicuous area of the shoes first to ensure you like the results. Feel free to contact us again with any other questions!
    Answered by: CUSTOMER SERVICE
    Date published: 2021-04-15

    why are they selected shoes a factory 2nd. Does that change how the shoe fits or wears?

    Asked by: Richard
    Factory Seconds are shoes with blemishes or defects sold at reduced prices. Cosmetic imperfections do not affect the fit of the shoe. You can learn more here: https://www.allenedmonds.com/factory-seconds-faq.html
    Answered by: CUSTOMER SERVICE
    Date published: 2020-05-15

    Are are the Wooster tan 12 D gone ?

    Asked by: Matt
    Unfortunately, if the size you prefer is not displayed or cannot be selected, it means it's not available to order. We're sorry for any disappointment. If you would like to view the current Factory Second loafers offered in size 12D, please follow this link: https://www.allenedmonds.com/sale/factory-second-shoes-boots/?prefn1=size&prefn2=styles&prefv3=D&prefv1=12&prefv2=Penny%20%26%20Venetian%20Loafer&prefn3=width We hope you find another color or style that you like!
    Answered by: CUSTOMER SERVICE
    Date published: 2020-01-09

    Will the Wooster Street Penny Loafer accommodate custom orthotics?

    Asked by: Larry
    Thank you for being an Allen Edmonds customer. Unfortunately, the Wooster Penny loafer does not have a removable insole. We apologize for the disappointment.
    Answered by: Allen Edmonds Consumer Services
    Date published: 2019-05-29
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