Handcrafted in the USA, with fine imported materials

Wooster Street Penny Loafer


Item# SF2288
$395.00 $199.97


  • Select Color 2289 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

    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

    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
    Wooster Street Penny Loafer is rated 4.3 out of 5 by 23.
    Rated 4 out of 5 by from Fit really well, comfortable. However the color is off It fits them same as Clark dress shoes and desert boots, as comfortable as dress shoes can be. However, the color is very different from what is shown in the pictures (I presumed the shoes in the picture is cleaned and shined.) And my left shoes has different shade from right one, expected better quality check from Allen Edmonds...
    Date published: 2020-12-15
    Rated 3 out of 5 by from Poor quality control Received a pair that should’ve been sent out as factory seconds. The leather color was awfully splotchy. Will be returning
    Date published: 2020-09-08
    Rated 5 out of 5 by from Absolutely love them My first pair of AE. Bought online wasn’t sure of shoe size in AE so I went with the same size as my sneakers size 11, so I order size 11 D. N it is a perfect fit all around . Didn’t have to break em in already comfortable . Can dress it up or down Must have
    Date published: 2020-06-29
    Rated 5 out of 5 by from Prettiest Pair Yet These are a beautiful pair of shoes. The cigar color is awesome. I just received a pair of Leeds in the same color. The pictures just don't do this color justice. Everything seems just right in the color matching, sewing and over all completion of the shoes. I wear a 10.5 EEE in the 65 last. These run just a tad narrow and shorter than the 65. Perhaps I should have gone for an 11 EEE, but I was afraid of my feet swimming in loafers. My right foot is slightly shorter than my left foot. The shoes fit my right foot snug but perfect. And it runs a tad short on my left foot. But, they are plenty wearable and I believe they will break in nicely. If you're in the market for an upscale loafer these will do the trick.
    Date published: 2020-06-26
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    • clientName_allenedmonds

    The front of my foot is a "D" width, but I have a narrow heel (probably a "C"). However, heels tend to vary by last. Do these run narrow?

    Heel width for a given overall shoe width (i.e. "D" width) tend to vary by last with some running narrower than others. I need a D-width made on a last that has a relatively narrow heel. (Italian shoes seem to be made this way.) How do the heels on Edmund Allen shoes run relative to the overall shoe width.
    Asked by: Ken

    What is the difference between the Wooster street loafer and the Mercer street loafer

    Asked by: Portdaddy1
    The difference is they are made a different lasts. The Wooster is 64 last and Mercer is made on the 78 last. -AE Consumer Care Dept.
    Answered by: Anonymous
    Date published: 2020-09-08

    What belts (and color) match this specific cigar color on the Wooster St?

    Asked by: jg
    I use the basic brown wide belt. It looks fine. Or you could try the coffee.
    Answered by: Matt
    Date published: 2020-06-26

    Can Wooster be made with a full rubber/composite sole?

    Asked by: R Gerald
    Unfortunately, this shoe can not be made with a full rubber sole. We apologize for any disappointment this may cause!
    Answered by: Anonymous
    Date published: 2020-03-03

    Where is the winter discount

    Asked by: Anonymous
    The Wooster is not apart of the winter sale. -AE Consumer Care Dept.
    Answered by: Anonymous
    Date published: 2020-02-14

    What color polish should I use on the cigar brown shoes?

    Asked by: LJ
    I used sapphire tobacco on mine. It works fine.
    Answered by: Matt
    Date published: 2020-06-29

    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
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