Handcrafted in the USA, with fine imported materials

Wooster Street Penny Loafer

$395.00 $295.00


Item# SF2288

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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

    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.

    Relaxed 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
    Wooster Street Penny Loafer is rated 4.3 out of 5 by 11.
    Rated 4 out of 5 by from One of my favorite Allen Edmonds shoes I have had these about six months now and given them some time to give a tested review. I ordered my usual size as I would for my 65 lasts (Strands, Park Avenue, etc.) and these fit true to size for me. They've been very comfortable from day 1 and these have become my favorite AE shoe. I wear these about once a week. I would have given these 5 stars except for one thing that happened with my shoes. A couple weeks ago, the rubber part of the heal on both shoes started to peel off and I had to glue them back down. Other than that, outstanding!
    Date published: 2019-10-10
    Rated 5 out of 5 by from The best It’s a great shoe.Comfortable and very good looking.i have all four in this style
    Date published: 2019-10-06
    Rated 4 out of 5 by from Great penny loafer Got this overseas through an online store, almost a blind buy but I usually love penny loafers. Men have less choice in terms of design but I'm thankful for that. These loafers are very comfy, fits me perfectly and basically have little complaints. And living in the far East, loafers are de rigueur for footwear as we need to take them off often when entering residences and at certain places. Before this, I've bought a pair of Nomads Chelsea boots (Factory Seconds) boots from AE before. In general these are well made shoes but IMHO a wee bit below the ones from Loake and RM Williams that I also have. However, I'm still very happy with these loafers and hope they will last..
    Date published: 2019-08-30
    Rated 5 out of 5 by from Fantastic design and feel. I have purchased more than 30 pairs of Allen Edmonds shoes. The Wooster is my new favorite.
    Date published: 2019-05-26
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    does this model come with a Dainite sole?

    Asked by: Anonymous
    Hello, Thank you for your inquiry! Unfortunately, we do not offer the Wooster with a Dainite sole. -AE Consumer Care Dept.
    Answered by: Anonymous
    Date published: 2019-10-03

    I am typically a Wide E shoe size & have Randolph, but want more comfortable shoe. Would a Wooster in D but relaxed fit work?

    I have never had luck upsizing from my size of 8.5 to a 9 in a regular shoe to try and compensate for extra needed width. My wife always says if you’re an 8.5E, then you need to find that size. The Randolph is just an uncomfortable shoe and I need a more comfy fit since I walk a lot in NYC. And I like a loafer and the sleeker look of the Wooster is more the style I want and the comfort style design sounds like it would be better. But it doesn’t come in E width, however it says relaxed fit. Would this Relaxed fit allow me to wear and 8.5D shoe?
    Asked by: SN
    Hello, Thank you for your inquiry! We recommend contacting our consumer care dept to assist you with sizing.
    Answered by: Anonymous
    Date published: 2019-09-30

    I normally wear the Corwallis in 11-1/2 D. For the Wooster Loafer what size should I get?

    Asked by: Anonymous
    Thank you for being an Allen Edmonds customer. Each style can fit differently based on the contours of your feet, so it’s difficult to recommend a size via email and guarantee a proper fit. Typically, we recommend trying the same size you usually wear and judging the fit based on how comfortable you feel in the shoes. If possible, we’d love to have you visit an Allen Edmonds retail store or one of our retail partners for a professional fitting. Our associates are trained to help you find the right fit for the various lasts and styles we offer. Also, keep in mind that products purchased on AllenEdmonds.com may be returned within 90 days, as long as the item is unworn and accompanied by the packing slip (we advise trying the shoes on a carpeted surface to keep them in returnable condition).
    Answered by: Allen Edmonds Consumer Services
    Date published: 2019-08-16

    Need narrow can you customize for additional charge?

    Need narrow Can you customize for me?
    Asked by: Anonymous

    I wear a 9 M. How does that relate to your width sizes?

    Asked by: keith
    Very narrow - runs small
    Answered by: T
    Date published: 2019-05-06

    which loafer has the widest toe box?

    Asked by: Anonymous
    You can try our Randolph penny loafer, it is built on the 79 last, which has a wide toe box area.
    Answered by: Bobbi
    Date published: 2019-04-11

    Is there a polish for this color?

    Asked by: Anonymous
    Thank you for reaching out to us. While we do not currently manufacture a Carbon polish, we would recommend using our Neutral polish.
    Answered by: Customer Service
    Date published: 2019-03-22

    What is the 64 last? I don't see it listed in the "All About Lasts" section.

    Asked by: Robert
    The 64 last is similar to the 65 last but with a chiseled shape. Feel free to contact us again if you have additional questions!
    Answered by: CUSTOMER SERVICE
    Date published: 2019-03-07
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