Handcrafted in the USA, with fine imported materials

Wooster Street Penny Loafer


Item# SF2288
$395.00 $199.97


  • Select Color 3161 Black

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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


    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
    Wooster Street Penny Loafer is rated 4.4 out of 5 by 25.
    Rated 5 out of 5 by from Fantastic Penny Loafer This is a fantastic penny loafer both in looks and fit. I have owned penny loafers from other makers and even from Allen Edmonds in other styles and lasts, and have had problems with them largely in their fit. However, this loafer style fits very well and looks great, a nice twist on the original penny loafer. I hope to purchase another color of the same style in the future, however want to wear this pair a while longer before deciding.
    Date published: 2021-08-06
    Rated 5 out of 5 by from Overall great buying experience Normally I do not purchase my footwear through the internet unless I have bought that brand before and know my size. Recently I purchased a Higgins Mill boot and Wooster Street loafer using the True Fit sizing guide on AE’s website, and I was surprised how accurate it is. 9EEE for the boots and 8.5EEE for the loafer and both fit perfectly. The Higgins Mills I bought is Chromexcel leather in Natural and I could not be happier. The boots fit perfectly, no break in time. I love the look of the Natural Chromexcel. This is one boot that I will wear all the time and will purchase again in another color. Quality is amazing. The Wooster loafer is also a great buy, can’t believe how the leather wrap around my feet and so soft and sometime if I don’t look down I wouldn’t have know I was wearing it. Overall you got a loyal AE customer for life. Great experience, great buy.
    Date published: 2021-05-15
    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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    When will this shoe be restocked?

    Asked by: Jackson
    Unfortunately, the Wooster st. is a close out style and we will not receive any new inventory. We apologize for any disappointment this may cause!
    Answered by: Anonymous
    Date published: 2021-04-12

    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

    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
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