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  5. Derby
(32)32

Penn Plain Toe Derby

Allen Edmonds

Men

$450.00Current Price $450.00
Color
Color: Black
Fit:True to size.
Size
D
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Details & care

Polished leather and a handcrafted build distinguish this plain-toe derby built with 360-degree Goodyear welt construction for lasting durability.

  • Lace-up style
  • 360° Goodyear welt construction allows for recrafting to extend the lift of the shoe
  • Leather upper lining, and sole
  • Made in the USA
  • Item #11372771
  • Core Product ID 333334E8XH

Size info

  • True to size.

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Allen Edmonds

Allen Edmonds has been creating timeless footwear in the U.S. since 1922. Today, the quality-obsessed shoe and accessories brand continues to produce exquisite styles using an impressively thorough 212-step process. With a focus on enduring fashion and unparalleled comfort, shoes are meticulously crafted from durable materials and available in a wide range of sizes and widths.

Reviews

(32)324.7 out of 5
Write a Review

Most helpful positive review

Oct 7, 2026

Wonderful WeatherProof Leather

Wonder full weatherproof brown Horween Chromexcel. The outsole is a bit beefy but you can replace that after purchase at a shoe repair store.
RoyBatty
Reposted from allenedmonds.com

Most helpful critical review

June 4, 2026
[This review was collected as part of a promotion.] The heel is short compared to my Black pair.. No type of shine. Too plain looking..
Stvn
Verified purchase
Reposted from allenedmonds.com

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5 stars81%
4 stars6%
3 stars9%
2 stars3%
1 star0%
Oct 7, 2026

Wonderful WeatherProof Leather

Wonder full weatherproof brown Horween Chromexcel. The outsole is a bit beefy but you can replace that after purchase at a shoe repair store.
Reposted from allenedmonds.com
RoyBatty
Oct 5, 2026

Great shoe....one issue: Quality

I love these shoes, they are comfortable and they look good. What I don't like is after only about 6 months a big chuck is coming off of the sole. AE normally is well known for quality so this was a huge disappointment.
Reposted from allenedmonds.com
allenedmonds.com response
We are so sorry that this has happened with your shoes. We understand your concern. We may have options for you regarding the shoes, if you could please contact us so we can go over those with you. You can find our contact details from this link, https://www.allenedmonds.com/help/contact-us. We appreciate your review and we have forwarded your comments to our Products Team. Thank you for your feedback.
Bad Shoe Quality
Sept 20, 2026

Weather ready.

[This review was collected as part of a promotion.] The weather proofing is a nice feature but I haven’t had the opportunity to test that yet. The stitches on top seem a bit loose or stretched. It’ll be interesting to see how the lighter St. Moritz sole holds up.
Reposted from allenedmonds.com
allenedmonds.com response
We are sorry for any issues with the stitching of the Penn Weather-ready Plain-toe Derby dress shoes. We understand your concern. We appreciate your review and we have forwarded your comments to our design team. We hope this is helpful for others. If you have any questions or concerns, you can find our contact details from this link, https://www.allenedmonds.com/help/contact-us. Thank you for your feedback.
Beefstew
Sept 1, 2026

Great Looking All Weather Shoes

These shoes look great either in jeans, khakis or slacks. It's soles will make sure that neither dsnow nor rain will stop you from getting to your appointment.
Reposted from allenedmonds.com
Verified purchase
Anonymous
Aug 2, 2026

My favorite dress shoes

[This review was collected as part of a promotion.] These are my favorite dress shoes ever! They are as comfortable as sneakers, but they can be dressed up or down with just about anything. The craftsmanship is superb, with visible stitching throughout. I have had them for a few months now, and they look as good as new. I love the traction on every terrain I have walked on, and it's nice to know that they are waterproof. I really look forward to wearing them because I haven't had a bad moment in them yet.
Reposted from allenedmonds.com
Verified purchase
storminn
July 21, 2026

Perfect for NorthEast Winter

[This review was collected as part of a promotion.] This Penn Waterproof Derby with the St Maritz Lug Sole is what I need when Commuting in the North East Winter. It is rugged enough to survive the snowy and icy sidewalks and steps of the metro, but still suitable for my office job, which requires I wear wool slacks and a sportcoat. The 2020 last is similar to the Trevor Derby and Dawson Chelsea I own, but with the whole new level of durability.
Reposted from allenedmonds.com
Verified purchase
Anonymous
July 21, 2026

Quality shoe, nice look, great price

Quite happy with these, I bought a pair in black and a second pair in brown on sale at a significant discount from regular pricing. Comfortable fit and I really like the look with the thick lugged soles and the clean look of the uppers. Waxed flat shoestrings are a bit awkward though they look great.
Reposted from allenedmonds.com
Verified purchase
AE addict
July 11, 2026

Bad weather companion.

I wondered about the possible weight of the St Moritz soles (evidently from a small Italian supplier) but they are lighter than a Danite-soled suede pair, but heavier than a same-sized leather-soled pair of AE shoes. Considering that the Penn is about 1" higher at the heel than a aimilar leather-soled pair, it seems that you don't pay a price in weight for suitabilty for a day with wet snow, and this pair was added to the collection with bad weather in mind. I'm in Florida and it's summer, so venturing into rain usually means cheap sneakers and I can't report on rain performance. Fit is predictably consistent in AE style; brand new, I need a shoehorn; this may cease as the pair breaks in. The Penn has a very clean look, with the brown welt contrasting nicely (and presumably fashionably) with the black leather and sole. My first try-on was with bare feet, and I can report that the interiors are very skin-friendly,
Reposted from allenedmonds.com
Verified purchase
ShoreDave
June 6, 2026

Classy and comfortable

[This review was collected as part of a promotion.]
Reposted from allenedmonds.com
Verified purchase
Inge
June 5, 2026

Great quality and really comfortable

As described on the website but better in person. They do take a few days to break in but once they are broken in they are very comfortable
Reposted from allenedmonds.com
Verified purchase
Mike Alley
June 4, 2026
[This review was collected as part of a promotion.] The heel is short compared to my Black pair.. No type of shine. Too plain looking..
Reposted from allenedmonds.com
Verified purchase
Stvn
May 14, 2026

One-Month Review of the Penn Weatherproof Plain-To

[This review was collected as part of a promotion.] After about a month of wearing the Penn Weatherproof Plain-Toe Derby Dress Shoes (a total of about 10 days), I can share the following impressions: 1) The shoes became comfortable after just one day. They did not require a substantial break-in period, which was a pleasant surprise. 2) Since the shoes have a bit of extra room, I added a summer insole, and it has worked well during warmer days, despite the shoes being weatherproof and seemingly designed more for colder seasons. I plan to continue wearing them during the hotter summer months to see how breathable and comfortable they remain. 3) I replaced the original laces with thinner ones to allow for more flexibility through the eyelets and to achieve a better fit. The original laces felt stiff and did not move smoothly through the holes, which made the shoes feel tighter. The thinner replacement laces noticeably improved the comfort for me, although this may simply be a personal preference. 4) I understand these shoes are more handmade compared to many mass-produced shoes on the market, but there are a few inconsistencies between the right and left shoes. For example, the outsole patterns are slightly different from one another. At first, I was concerned this might affect comfort or performance, but I assume Allen Edmonds checked the shoes to ensure they met functional standards. 5) Another noticeable difference is the vertical leather strip at the back of the shoes (about 3/4 inch wide) that reinforces the heel. On one shoe, the strip is visibly offset compared to the other, making the two shoes look somewhat different. Personally, I did not mind this too much, as some people consider such variations evidence of genuine handmade craftsmanship. Still, it could also be viewed as a quality-control issue. In terms of appearance, I think these are great-looking shoes, and I have received many compliments while wearing them. The design works well for both business casual and more formal settings. Overall, I am satisfied with the shoes and currently would rate them around 93 out of 100. If they continue to hold up well over time, I would likely rate them even higher. The quality of the leather and craftsmanship give me confidence that these shoes can last a long time and eventually be resoled. If that proves true, I would definitely consider purchasing another pair in a different color.
Reposted from allenedmonds.com
Verified purchase
LoveSnow
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    Allen Edmonds
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    Nordstrom
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    Created by nordstromstyling
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    Nordstrom
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    Allen Edmonds
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    Created by nordstromstyling
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    FERRAGAMO
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    Jack Victor
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    Polo Ralph Lauren
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Early Black Friday Sale: up to 25% off select fashion.Early Black Friday Sale: up to 25% off select fashion.

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Sounds Like Fun!

Make time to make merry with joyful events happening in our stores, from photos with Santa to holiday breakfast.
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