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This hour's deals
Allen Edmonds
Allen Edmonds Windsor Derby Leather
−45%
Shoes · Allen Edmonds

Allen Edmonds derby that dresses up jeans or a suit

Allen Edmonds Windsor Derby Leather

The Windsor Derby in leather from Allen Edmonds, a staple for the guy building a serious shoe rotation.

Deal score 6.5 · Great deal
$249.00$450.00 Allen Edmonds's regular price

You save $201.00 at Allen Edmonds

Deal.ai's agents found this deal on November 9. The store may have changed its price since.

Why it's a great deal

  • Elsewhere right now: Nordstrom $450.00, Bloomingdale's $450.00 (typical $450.00 across 2 stores)
  • Allen Edmonds lists its regular price at $450.00: 45% off by its own figures
  • Rated 4.4 out of 5 by 231 buyers
Visit Allen Edmonds

Every store we checked

  • Allen EdmondsNew

    In stock

    $249.00Observed at 12:48 AM
    Visit Allen Edmonds
  • Allen EdmondsNew

    In stock

    $269.00Free shippingObserved at 12:49 AM
    Visit Allen Edmonds
  • NordstromNew

    In stock

    $450.00Observed at 12:48 AM
    Visit Nordstrom
  • 888Lots.comNew

    Availability unknown

    $165.00Observed Nov 6, 2026, 9:47 PM
    Visit 888Lots.com
  • Bloomingdale'sNew

    Availability unknown

    $450.00Observed at 12:48 AM
    Visit Bloomingdale's
  • Sherman Brothers ShoesNew

    Availability unknown

    $450.00Observed at 12:48 AM
    Visit Sherman Brothers Shoes
  • LystNew

    Availability unknown

    $450.00Observed at 12:48 AM
    Visit Lyst
  • EditorialistNew

    Availability unknown

    $450.00Observed at 12:48 AM
    Visit Editorialist

Store links may earn us a commission. Some prices via Klarna.

Price history and every store's price →

Reading Allen Edmonds’s product page for the details…

Specs

Gender
MALE, Men's
Boot Style
Oxfords
Type
Derby shoe
Closure Style
Lace-up
Material
Leather
Leather Material
Vegetable-tanned leather (soles), Premium leather, Premium leather (uppers)
Occasion
Dress Shoe
Outsole Material
Leather
Age Group
Adult
Department
Men's

About the Allen Edmonds Windsor Derby Leather

The Allen Edmonds Windsor is a men's plain-toe derby in premium leather with a leather lining and a double-layer vegetable-tanned leather sole. It is a dress shoe built for stability, with Allen Edmonds' CustomCork insole that molds to the foot, and the sole can be recrafted by the company. It sits among Allen Edmonds' classic dress shoes as a roomier, easier-on alternative to a closed-lacing oxford, and owners rate it well for its leather and clean shape while noting a stiff break-in and the care a leather sole needs.

Best forMen who wear suits or dress trousers to workBuyers who want a resolable, recraftable leather shoeShoppers who prefer a roomier derby lacing over an oxfordWide or hard-to-fit feet, given Allen Edmonds' size range
Pros
  • Plain-toe derby lacing opens wider and fits a higher instep than an oxford
  • Premium leather uppers with a full leather lining
  • CustomCork insole molds to the foot over time
  • Double-layer vegetable-tanned leather sole can be recrafted by Allen Edmonds
  • Classic, clean-lined shape that suits business dress

More deals like this

  • All Allen Edmonds deals and products
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  • All Bloomingdale's deals and prices
  • All Lyst deals and prices
  • Early Black Friday Shoe Deals 2026

Price facts

  • This deal was $249.00 at Allen Edmonds on Nov 9.
  • Last seen at $165.00 at 888Lots.com on Nov 6.
  • Checked at 8 stores.

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Cons
  • Leather soles are slick on wet pavement and wear faster than rubber
  • Needs shoe trees and regular polishing to hold shape
  • Break-in takes time; the stiff leather sole can feel hard at first
  • Runs narrow for some buyers

What reviewers say

  • 4.4 / 5231 ratings

Rated 4.3 out of 5 from 185 ratings, the Windsor is generally well regarded for its leather, fit and classic look. Complaints center on stiffness out of the box and the care a leather-soled dress shoe demands.

What people mention
  • Leather qualityPraisedOwners describe the uppers as supple premium leather that polishes up well.
  • Break-inMixedSeveral say the shoe is stiff at first and comfortable only after a few wears.
  • SoleMixedThe leather sole is praised for being resolable but called slippery and fast-wearing outdoors.
  • FitMixedMany find the derby lacing roomy, while some say it runs narrow.

Questions and answers

Is the Windsor a derby or an oxford?
It is a plain-toe derby, so the lacing panels sit on top of the vamp and open wider than an oxford's. That makes it easier to get on and more forgiving over a high instep.
Can the sole be replaced?
Yes. The double-layer vegetable-tanned leather sole is resolable, and Allen Edmonds recrafts the shoe at its own facility.
How does it fit?
It is a leather-lined dress shoe on a stability-focused sole, and the derby lacing gives some room. Try your usual Allen Edmonds size; buyers who find it narrow should size up in width.
How should I care for it?
Use shoe trees after each wear, brush off dirt, and polish the leather regularly. Keep the leather sole dry and avoid heavy wear in rain.
What is the CustomCork insole?
It is a cork footbed that compresses and molds to the shape of your foot with wear, which is why the shoe gets more comfortable over time.
How does the Windsor compare with the Park Avenue?
The Park Avenue is a closed-lacing cap-toe oxford, so it is dressier and less forgiving over a high instep. The Windsor's open derby lacing is roomier and easier to put on, at the cost of a slightly less formal look.

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