Is $59.99 a good price for the Jaylon Chelsea boot?

It is the best new price among the 4 stores that sell it new, at $59.99 at ShopSimon as of November 8, 2026. That is low for a leather-lined Chelsea boot.

How does the Jaylon fit?

It runs true to length for most buyers but narrow for some. If you have wide feet, size up a half size.

What is the heel height?

The heel is 1.25 inches, a standard dress-boot height.

What is the upper made of?

The upper is leather with a leather lining, a foam insole and a rubber and EVA outsole.

What sizes are available?

US men's sizes 6 to 14, including half sizes from 6.5 to 11.5.

Is it only available in gray?

Yes. Gray is the only color offered.

Where is the Thomas & Vine Jaylon Cap Toe Chelsea Boot cheapest?

At ShopSimon, for $59.99, as of our latest check.

What do buyers say about the Thomas & Vine Jaylon Cap Toe Chelsea Boot?

Rated 4 out of 5 from 17 ratings.

Where can I buy the Thomas & Vine Jaylon Cap Toe Chelsea Boot?

4 stores we checked sell it, including Walmart, Shop Simon, ShopSimon, Target.

Thomas & Vine Jaylon Cap Toe Chelsea Boot

Best price now

$59.99at ShopSimonObserved at 7:08 AM

Compared across 4 stores. Prices are checked against each store and labelled with when.

Visit ShopSimon

Thomas & Vine Jaylon Cap Toe Chelsea Boot

Best price now

$59.99at ShopSimonObserved at 7:08 AM

Compared across 4 stores. Prices are checked against each store and labelled with when.

Visit ShopSimon

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Our take on the Thomas & Vine Jaylon Cap Toe Chelsea Boot

The Thomas & Vine Jaylon is a men's Chelsea boot in gray leather with a cap toe, elastic side panels and a pull tab. It has a leather lining, a foam insole and a rubber and EVA outsole, with a 1.25-inch heel. The best new price is $59.99 at ShopSimon as of November 8, 2026, and 4 stores sell it new.

Best forMen who want a dress-casual Chelsea bootWearers who need wide size runs up to 14Buyers on a budgetFall and winter everyday wear

Pros

Full leather upper with leather lining
Cap toe gives a dressier look than a plain Chelsea
Foam insole adds cushioning underfoot
Rubber and EVA outsole grips well on pavement
Sizes run from 6 to 14, including half sizes

Cons

Only one color: gray
Elastic side panels can loosen over time
Leather upper needs care to hold its shape
Limited feedback so far, 17 ratings

Thomas & Vine Jaylon Cap Toe Chelsea Boot prices at every store

ShopSimonNew
In stock
$59.99Observed at 7:08 AM
Visit ShopSimon
Shop SimonNew
In stock
$59.99+ $4.95 shippingObserved at 7:08 AM
Visit Shop Simon
WalmartNew
In stockSold by KNS International
$139.99Verified
Visit Walmart
TargetNew
Out of stock
$59.99Observed at 7:08 AM
Visit Target

Also available at

WalmartCheck price at Walmart

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

Thomas & Vine Jaylon Cap Toe Chelsea Boot price history

Lowest price we've seen: $59.99 on Nov 8 at ShopSimon. Tracked across 4 stores since Nov 8.

What reviewers say

4 / 517 ratings

Ratings average 4 out of 5 from 17 buyers. Owners mostly like the look and the price for a leather boot.

What people mention

ValuePraisedBuyers say the leather upper looks and feels better than the price suggests.
ComfortPraisedThe foam insole and leather lining are called comfortable for all-day wear.
FitMixedSome buyers find the fit narrow and suggest sizing up.
Color optionsCriticisedShoppers wish it came in more than gray.

About the Thomas & Vine Jaylon Cap Toe Chelsea Boot

This is a practical pair of chelsea boots from Thomas & Vine that is made in men's sizes. They come in just one color: gray.

Specifications

Manufacturer Color: GreySource
Color: GraySource
Outsole: Rubber, EVASource
Age Group: AdultSource
Lining

Questions and answers

Is $59.99 a good price for the Jaylon Chelsea boot?: It is the best new price among the 4 stores that sell it new, at $59.99 at ShopSimon as of November 8, 2026. That is low for a leather-lined Chelsea boot.
How does the Jaylon fit?: It runs true to length for most buyers but narrow for some. If you have wide feet, size up a half size.
What is the heel height?: The heel is 1.25 inches, a standard dress-boot height.
What is the upper made of?: The upper is leather with a leather lining, a foam insole and a rubber and EVA outsole.
What sizes are available?: US men's sizes 6 to 14, including half sizes from 6.5 to 11.5.
Is it only available in gray?: Yes. Gray is the only color offered.
Where is the Thomas & Vine Jaylon Cap Toe Chelsea Boot cheapest?: At ShopSimon, for $59.99, as of our latest check.
What do buyers say about the Thomas & Vine Jaylon Cap Toe Chelsea Boot?: Rated 4 out of 5 from 17 ratings.
Where can I buy the Thomas & Vine Jaylon Cap Toe Chelsea Boot?: 4 stores we checked sell it, including Walmart, Shop Simon, ShopSimon, Target.