Cavanaugh Penny Loafer


Cavanaugh Penny Loafer



Item# SF50021


  • Select Color: 50021 Black

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Details & Overview

Cavanaugh Penny Loafer


  • Slip-on loafer dress shoes
  • Moc-toe pinch penny loafers
  • Lined premium calfskin leather or suede leather upper
  • Single oak leather sole with regular heel - All about Soles
  • Handsewn construction - 212 steps of Craftsmanship
  • Manufactured on the Handsewn 114 Last - All about Lasts
  • Proudly handcrafted in the USA of fine imported leathers at our Port Washington, Wisconsin factory


Whether it’s money or style — change is good. That’s why we took our traditional pinch penny and gave it a broader toe plug. The result is a contemporary loafer with artisan touches that will have you looking like a million cents.

Product Care

Allen Edmonds Shoe Care

When caring for your calfskin, use Allen Edmonds Leather Lotion to remove surface residue and to keep leather soft and pliable. To achieve a fine luster, wipe shoes with a damp cloth and allow them to air dry at room temperature. Then, apply a coat of Allen Edmonds Premium Shoe Polish with a cloth or horsehair dauber and allow to air dry.

Further details and videos are available on our Caring for Your Shoes page.

Cavanaugh Penny Loafers is rated 3.6 out of 5 by 130.
Rated 5 out of 5 by from Fantastic quality !! These shoes last for years...well worth the money !!
Date published: 2017-09-13
Rated 2 out of 5 by from Stitching doesn't hold up I only buy Allen Edmond shoes ... have 5 pairs ... and have always been extremely satisfied until the Cavenaugh's. Have had these shoes for ~12 months. 6 months ago the stitching on the uppers of one shoe started to stretch. Now has gotten to the point they appear to ready to fully separate. Definitely didn't come from overuse or ill fitting since I wear them only 1 time a week and the shoes fit properly. Hate it since I really like how they look and have gotten compliments on them. Guess I will just have to replace them with a pair of Weejuns ... at half the price..
Date published: 2017-08-10
Rated 2 out of 5 by from Really wanted these to work, but cannot wear Picked up a pair of 11 D in Oxblood, and they look absolutely amazing. However, I cannot wear these without being uncomfortable all day long, which is horrible for a pair of loafers. These pinch bad, even though I was assured by the salesperson that the moccasins would relax. Further, the sole is so inflexible that I thud around the office. After wearing 7 times these will remain in the closet and not worn. I own several pairs of AE, and will purchase more. But, the Cavanaugh truly disappoints.
Date published: 2017-07-28
Rated 5 out of 5 by from Solid, comfy shoe. A little narrow First, I wear a size 9.5 3E. These are a bit narrow when compared to the fifth aves that fit me perfectly. The 9.5 cav fits my heel perfect but the widest area of the shoe was too narrow. I moved up to a 10 3E and its comfortable, but the heel is a little loose. All in all its worth it. Beautiful quality and a very comfortable, smooth feeling loafer. Just wish I couldve gotten both a wider box and narrow heel, but again...Im a 3E so take that for what it's worth. Id buy again.
Date published: 2017-07-27
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Ask & Answer

I have over pronation. Does the Cavanaugh have a replaceable insole to provide more arch support?

Asked by: Carl202
The Cavanaugh does not feature removable insoles. Here's the link to the styles we offer that accommodate custom orthotics: It is vitally important to visit an Allen Edmonds retail store or retail partner for a professional fitting to increase your chances of being fit correctly for each last and style. However, keep in mind that products purchased on may be returned at any time, as long as the item is unused and accompanied by the packing slip.  Trying the shoes on a carpeted surface will help prevent scuffing on the sole and keep the shoes in returnable condition.
Date published: 2017-07-25

Is this shoe recraftable? Thank you.

Asked by: Anonymous
These shoes are brand new. I have tried them on, but never actually worn them. If you mean, do I know whether AE will refurbish them for me when they wear out, I suspect "Yes", but I am not certain.
Answered by: L3
Date published: 2017-09-05

What would be the best color sole dressing to use for the oak heal on brown calfskin cavanaugh loafers?

Asked by: Ryan
We recommend Brown Heel and Sole Edge Dressing. Feel free to contact us with any additional questions.
Date published: 2017-03-13

Does this shoe have the layer of cork between the insole and the outsole like most of your other dress shoes?

Asked by: KP
To my understanding, it does not. Only the welted construction have the cork layer. The Cavanaugh is a handsewn construction.
Answered by: Weber
Date published: 2016-11-19

how do you clean the suede shoes

Asked by: martin
For everyday cleaning and care of your suede shoes, we recommend using our Suede Cleaning System. We also recommend our Suede Spray Waterproofer to help protect them from stains and water. Please feel free to contact us with any additional questions.
Date published: 2016-04-18

What suede belt matches the snuff suede cavanaugh penny loafer?

Asked by: Patty17
We recommend the Wide Basic Dress Belt in Brogue Suede #39537. Please feel free to contact us with any additional questions.
Date published: 2016-01-28

Will the olive suede be available in narrow widths?

I have a narrow foot, and would really like to have the suede version of this shoe. Are there plans to produce it in a B width?
Asked by: Alex
Yes, some sizes will be available in a B width. They are not in stock at this time but can be backordered. Please feel free to contact our customer service team directly at or 1-877-817-7615 (Mon-Fri 7:00AM-8PM CST) and they can assist you in placing an order.
Date published: 2015-10-06

Oxblood matching belt

What color belt would you recommend to pair with the oxblood cavanaughs?
Asked by: Dt1988
We recommend pairing your Oxblood Cavanaugh style with the Dupont Ave belt in Oxblood. Please feel free to contact us with any further questions.
Date published: 2015-06-18

What color Wide Basic Dress Belt would be a better match for the brown Cavanaugh? The dark brown or brown belt?

Asked by: Anonymous
We recommend pairing your Cavanaugh loafers in Brown leather with the Wide Basic Dress Belt in Dark Brown. Please feel free to contact us with any additional questions.
Date published: 2015-04-23

Are all allenedmonds shoes goodyear welted?

For instance this model.
Asked by: Bob
The Cavanaugh style is not Goodyear welted loafer. To find out which styles use the Welted, Handsewn, or Bologna construction you can check out their bullet-point details in the description of each shoe. You can also filter by welted styles by clicking on 'Shoes', then using the filter menu on the left-hand size of the webpage, clicking on 'Construction' and checking the box for '360 Welted Shoes'. We recommend checking our the following welted loafers: the Randolph, the Ascher, and the Patriot. Please feel free to contact us with any additional questions.
Date published: 2015-03-30
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View with Pants

Cavanaugh Penny Loafer

Select Color:

  • 50021 Black
  • 50023 Brown
  • 50025 Walnut
  • 50026 Oxblood

Select Pant:

Cavanaugh Penny Loafer, 50021 Black, blockout
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Cavanaugh Penny Loafer, 50021 Black, blockout

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