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(114)114

Windsor Plain Toe Derby

Allen Edmonds

Men

Current Price $450.00
Color
Color: Chili
Fit:True to size.
Size
Width
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Details & care

Vegetable-tanned leather and a minimalist plain-toe design highlight the impeccable craftsmanship of this handcrafted all-American derby. A responsive CustomCork insole delivers ultimate comfort for day-long wear.

  • Leather upper, lining and sole
  • Made in the USA
  • Item #10551075
  • Core Product ID 333333LQZA

Size info

  • True to size.
  • D(medium).

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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

(114)1144.5 out of 5
Write a Review

Most helpful positive review

Aug 26, 2026

Excellent Style and Fit

As always, Allen Edmonds shoes are great fit, and styled in a way that I can count on. Love the shoes, love the quality.
CEric
Verified purchase
Reposted from allenedmonds.com

Most helpful critical review

Aug 24, 2026

Most Uncomfortable Shoes Ever!

I thought I’d splurge on nice new shoes for my wedding… these are the most uncomfortable shoes I’ve ever worn. I broke them in a few times and even tried adding inserts - nothing helped. Ended up changing shoes with my brother on the day. So disappointed and I will not be purchasing Allen Edmonds again.
Mschwartzy
Reposted from allenedmonds.com
allenedmonds.com response
We are so sorry that the Windsor Plain-tow Derby dress shoes have caused such discomfort. We understand how disappointing that is. We appreciate your review and we have forwarded your comments to our Products Team. We hope this is helpful for others. If you have any questions or concerns, please call our AllenEdmonds.com Consumer Care Department at 1-877-817-7615. The Call Center hours of operation are Monday-Friday 9:00a.m.-6:00p.m. and Saturday 10:00a.m.-5:00p.m. CT. Thank you for your feedback.

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5 stars76%
4 stars11%
3 stars5%
2 stars4%
1 star4%
Aug 30, 2026

Great shoe.

[This review was collected as part of a promotion.] High quality shoe, but it runs about a 1/2 to a full size long and is generally narrow. I purchased my normal size as the description recommended but had to send the first pair back for a smaller wider pair. There was a small spot (size of a grain of sand) on the leather that was missing polish that I had to touch up and the edge of the sole has a small imperfection that needed edge dressing.
Reposted from allenedmonds.com
Verified purchase
BE84
Aug 27, 2026

Runs A Bit Slim

Shoe seems to be very narrow and small. I do not have wide feet.
Reposted from allenedmonds.com
allenedmonds.com response
We are so sorry that the Windsor Plain-toe Derby dress shoes are tighter than expected. We understand how disappointing that is. We appreciate your review and we have forwarded your comments to our Products 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.
Verified purchase
MC55
Aug 26, 2026

Excellent Style and Fit

As always, Allen Edmonds shoes are great fit, and styled in a way that I can count on. Love the shoes, love the quality.
Reposted from allenedmonds.com
Verified purchase
CEric
Aug 24, 2026

Most Uncomfortable Shoes Ever!

I thought I’d splurge on nice new shoes for my wedding… these are the most uncomfortable shoes I’ve ever worn. I broke them in a few times and even tried adding inserts - nothing helped. Ended up changing shoes with my brother on the day. So disappointed and I will not be purchasing Allen Edmonds again.
Reposted from allenedmonds.com
allenedmonds.com response
We are so sorry that the Windsor Plain-tow Derby dress shoes have caused such discomfort. We understand how disappointing that is. We appreciate your review and we have forwarded your comments to our Products Team. We hope this is helpful for others. If you have any questions or concerns, please call our AllenEdmonds.com Consumer Care Department at 1-877-817-7615. The Call Center hours of operation are Monday-Friday 9:00a.m.-6:00p.m. and Saturday 10:00a.m.-5:00p.m. CT. Thank you for your feedback.
Mschwartzy
Aug 3, 2026

Most comfortable dress shoes

I've had these shoes for a couple months now and they have kept their shape and form very well. They are the most comfortable dress shoes I own and fit incredibly well. The quality of construction is very apparent in the stitching and weld work.
Reposted from allenedmonds.com
Verified purchase
NRobB
Aug 2, 2026

Great Fit and Comfortable!

Very happy with this purchase. The shoes feel sturdy without being heavy. I’ve worn them for long and my feet stayed comfortable the entire time throughout.
Reposted from allenedmonds.com
ABAB
July 26, 2026

A classic

[This review was collected as part of a promotion.] This is the second pair of this shoe that I own (the other is chili brown). Timeless style with a comfortable fit out of the box. A tremendous value; I will be well served by this shoe for many years.
Reposted from allenedmonds.com
Verified purchase
Aten
July 13, 2026
[This review was collected as part of a promotion.] Great shoe, beautiful finish in chili leather and quite comfortable. I would, however, have appreciated a slightly narrower option for a more perfect fit, although it wasn't a deal breaker for me.
Reposted from allenedmonds.com
Augustine
June 27, 2026

Typically great

[This review was collected as part of a promotion.] Usual Allen Edmonds high quality. Takes a bit to break in but checks all the boxes for an NYC finance professional
Reposted from allenedmonds.com
Verified purchase
Clive
June 27, 2026

Poor leather quality

I expected the leather to be a much softer quality
Reposted from Allen Edmonds
Allen Edmonds response
We value your feedback on the Windsor Clean-Toe Derby and have forwarded this information to the appropriate team. If you need further assistance, please don't hesitate to contact our Consumer Care Department. You can find our contact information here: https://www.allenedmonds.ca/en/help/contact-us?icid=BottomNav_ContactUs
Verified purchase
Maxie
June 24, 2026
Good fit, I’m usually size 12, ended up taking size 11. Comfortable, well made
Reposted from Allen Edmonds
Verified purchase
Perry
June 21, 2026

Nice

The, as yet unworn shoes, appear to be in very good condition with no apparent defects.
Reposted from allenedmonds.com
Verified purchase
TTTT123456

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