Is the Keelan worth buying at $91.99?

At $91.99 at eBay as of November 3, 2026, it is well below typical Stuart Weitzman boot pricing. That makes it a strong value if the over-the-knee fit works for your calf.

How does the Keelan compare with a heeled over-the-knee boot?

The Keelan has no heel, so it is flatter and easier to walk in than heeled over-the-knee styles. You give up height and a dressier line.

Will the 19.3-inch shaft fit over my knee?

The 19.3-inch shaft is designed to sit over the knee on most wearers. Fit depends on your leg length and calf; check the calf circumference before ordering.

What is the Keelan made of?

It uses genuine leather or suede on the upper, a leather lining and a rubber outsole. The black colorways come in nappa leather and smooth leather.

When is the Keelan cheapest?

The lowest price seen since October 30, 2026 was $91.99 at eBay, and no higher price has been recorded in that window. Watch for end-of-season clearance for further drops.

What comes in the box?

You get the pair of boots; Stuart Weitzman typically includes a dust bag with its boots. Confirm contents with the individual seller.

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Shoes · ShopSimon

Stuart Weitzman leather, made to stride

Name: Stuart Weitzman Keelan Leather Boot
Brand: Stuart Weitzman

Stuart Weitzman Keelan Leather Boot

The Keelan leather boot from Stuart Weitzman for anyone investing in a boot that lasts seasons.

Deal score 6.1 · Great deal

$441.75$750.00 ShopSimon's regular price

You save $308.25 at ShopSimon

Deal.ai's agents found this deal on November 5. The store may have changed its price since.

Why it's a great deal

ShopSimon lists its regular price at $750.00: 41% off by its own figures

Visit ShopSimon

Every store we checked

ShopSimonNew
In stock
$441.75Observed at 10:17 AM
Visit store
eBayNew
Availability unknownSold by hottercooler
$299.99Observed at 10:17 AM
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Lux LairNew
Availability unknown
$372.00Observed at 10:17 AM
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BlueflyNew
Availability unknown
$477.00Observed at 10:17 AM
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PoshmarkNew
Availability unknown
$477.00Observed at 10:17 AM
Visit store

Price history and every store's price →

Reading ShopSimon’s product page for the details…

Specs

Width: Width Medium
Material: Genuine Leather, Genuine Suede, Rubber
Heel Height: No Heel
Heel Style: Block
Color: Black Nappa Leather, Black Leather
Shaft Height: Over-the-knee
Style: Casual
Season: Spring, Winter, Fall
Support Type: Cushioning
Outsole Material: Rubber Outsole

About the Stuart Weitzman Keelan Leather Boot

The Stuart Weitzman Keelan is an over-the-knee leather boot with a flat block heel, a 19.3-inch shaft and a leather lining. It is built for everyday fall and winter wear rather than dressy occasions, and the rubber outsole adds grip on wet pavement. The best new price is $91.99 at eBay as of November 3, 2026, the only price seen across three stores since October 30, 2026, so there is no recent range to compare against.

Best forShoppers who want an over-the-knee silhouette without a high heelFall and winter wear with jeans, leggings or midi skirtsBuyers who prefer genuine leather and a leather liningAnyone wanting a flat, walkable tall boot at a low price

Pros

Genuine leather upper with a full leather lining
Flat block heel keeps it comfortable for long wear
19.3-inch shaft gives true over-the-knee coverage
Rubber outsole adds traction in wet weather
Rated 4.5 out of 5 from 203 ratings

Cons

More deals like this

More from Stuart Weitzman

All Travel Tech Clothes Shoes Jewelry Home Beauty Outdoors Toys

This hour's deals

−41%

Shoes · ShopSimon

Stuart Weitzman leather, made to stride

Stuart Weitzman Keelan Leather Boot

The Keelan leather boot from Stuart Weitzman for anyone investing in a boot that lasts seasons.

Deal score 6.1 · Great deal

$441.75$750.00 ShopSimon's regular price

You save $308.25 at ShopSimon

Deal.ai's agents found this deal on November 5. The store may have changed its price since.

Why it's a great deal

ShopSimon lists its regular price at $750.00: 41% off by its own figures

Visit ShopSimon

Every store we checked

ShopSimonNew
In stock
$441.75Observed at 10:17 AM
Visit store
eBayNew
Availability unknownSold by hottercooler
$299.99Observed at 10:17 AM
Visit store
Lux LairNew
Availability unknown
$372.00Observed at 10:17 AM
Visit store
BlueflyNew
Availability unknown
$477.00Observed at 10:17 AM
Visit store
PoshmarkNew
Availability unknown
$477.00Observed at 10:17 AM
Visit store

Price history and every store's price →

Reading ShopSimon’s product page for the details…

Specs

Width: Width Medium
Material: Genuine Leather, Genuine Suede, Rubber
Heel Height: No Heel
Heel Style: Block
Color: Black Nappa Leather, Black Leather
Shaft Height: Over-the-knee
Style: Casual
Season: Spring, Winter, Fall
Support Type: Cushioning
Outsole Material: Rubber Outsole

About the Stuart Weitzman Keelan Leather Boot

Pros

Genuine leather upper with a full leather lining
Flat block heel keeps it comfortable for long wear
19.3-inch shaft gives true over-the-knee coverage
Rubber outsole adds traction in wet weather
Rated 4.5 out of 5 from 203 ratings

Cons

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Ask our agent about this deal

It checks today's price at every store, compares the alternatives and answers in about a minute.

What reviewers say

Owners rate the Keelan highly, at 4.5 out of 5 from 203 ratings, and most praise the soft leather and the flat, walkable sole. Fit over the calf is the most common complaint.

Pros

Soft, supple leather that breaks in quickly
Comfortable flat block heel for all-day wear
Shaft stays up over the knee
Looks polished with casual outfits

Cons

Tight fit over larger calves
Shaft can slouch or bunch on shorter legs
Leather shows scuffs and needs care

Questions and answers

Is the Keelan worth buying at $91.99?: At $91.99 at eBay as of November 3, 2026, it is well below typical Stuart Weitzman boot pricing. That makes it a strong value if the over-the-knee fit works for your calf.
How does the Keelan compare with a heeled over-the-knee boot?: The Keelan has no heel, so it is flatter and easier to walk in than heeled over-the-knee styles. You give up height and a dressier line.
Will the 19.3-inch shaft fit over my knee?: The 19.3-inch shaft is designed to sit over the knee on most wearers. Fit depends on your leg length and calf; check the calf circumference before ordering.
What is the Keelan made of?: It uses genuine leather or suede on the upper, a leather lining and a rubber outsole. The black colorways come in nappa leather and smooth leather.
When is the Keelan cheapest?: The lowest price seen since October 30, 2026 was $91.99 at eBay, and no higher price has been recorded in that window. Watch for end-of-season clearance for further drops.
What comes in the box?: You get the pair of boots; Stuart Weitzman typically includes a dust bag with its boots. Confirm contents with the individual seller.