Is the Eastland Ryan good for everyday wear?

Yes. It is a casual leather ankle boot with a padded insole and a low heel, suited to daily wear with jeans or chinos. It is not built for heavy work or rough terrain.

Does the Ryan run true to size?

Eastland handsewn boots generally fit close to standard shoe size, and the leather loosens with wear. If you are between sizes or plan thick socks, consider going up half a size.

No. The leather upper is not sealed against water, so it handles light damp but not rain or snow. Treat the leather and avoid deep puddles.

How does it compare with a taller moc-toe boot?

The Ryan is a low ankle boot, so it is lighter and easier to pair with casual outfits, but it gives less ankle support and coverage than a taller moc-toe boot.

What is the heel and shaft height?

The heel is about 1.125 inches and the shaft about 5 inches, with a boot circumference of roughly 12 inches. That makes it a low-profile ankle boot.

Can the sole be replaced?

The rubber sole is cemented rather than stitched, so a cobbler can usually resole it, though many owners simply replace the boots when the sole wears through.

Where is the Eastland Ryan Leather Boot cheapest?

At Kohl's, for $74.80, as of our latest check.

Where can I buy the Eastland Ryan Leather Boot?

16 stores we checked sell it, including Shop Simon, Gilt, Famous Footwear, DSW, Tractor Supply Co.

Eastland Ryan Leather Boot

Best price now

$74.80at Kohl'sChecked 7 h ago

Compared across 17 stores. Prices are checked against each store and labelled with when.

Visit Kohl's

Eastland Ryan Leather Boot

Best price now

$74.80at Kohl'sChecked 7 h ago

Compared across 17 stores. Prices are checked against each store and labelled with when.

Visit Kohl's

Ask our agent about this product

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

Price facts

Lowest price today: $74.80 at Kohl's (checked Nov 15, 2026).
Checked at 17 stores.

Our take on the Eastland Ryan Leather Boot

The Eastland Ryan is a men's ankle boot in leather with a moc-toe front, a padded collar and a pull tab at the heel. It sits on a rubber sole with a padded insole and a modest heel, so it works as a casual everyday boot rather than a work boot. It suits shoppers who want a handsewn moc-toe look without the bulk of a taller boot. Against similar moc-toe boots, it leans dressier and lighter; owners of Eastland handsewn styles generally praise the leather and comfort but note the soles wear faster than heavier lug boots.

Best forEveryday casual wear with jeans or chinosShoppers who want a moc-toe boot in a low ankle heightFall and mild-winter city wearMen who prefer lace-up boots over slip-ons

Pros

Handsewn moc-toe stitching gives a distinctive look
Leather upper with a padded collar for ankle comfort
Padded insole adds cushioning underfoot
Rubber sole with a low heel keeps it easy to walk in
Pull-on tab helps get the boot on

Cons

Not waterproof; leather needs care in wet weather
Rubber sole offers limited traction on ice or mud
Ankle height gives little support compared with taller boots
Moc-toe stitching can scuff and show wear

Eastland Ryan Leather Boot prices at every store

Kohl'sNew
In stock
$74.80Free shippingChecked 7 h ago
Visit Kohl's
JCPenneyNew
In stock
$77.00Free shippingChecked 7 h ago
Visit JCPenney
Shop SimonNew
In stock
$74.98+ $4.95 shippingChecked 7 h ago
Visit Shop Simon
WalmartNew
In stockSold by La ViaReturns: Sold by a Walmart Marketplace seller; returns go to the seller under the seller's returns policy.
$79.99Free shippingChecked 7 h ago
Visit Walmart
DSWNew
In stock
$76.99+ $7.95 shippingChecked 7 h ago
Visit DSW
GiltNew
In stock
$79.99+ $11.99 shippingChecked 7 h ago
Visit Gilt
Gilt.comNew
In stock
$79.99+ $11.99 shippingChecked 7 h ago
Visit Gilt.com
NordstromNew
In stock
$110.00Free shippingChecked 7 h ago
Visit Nordstrom
Tractor Supply CoNew
In stock
$110.99Free shippingChecked 7 h ago
Visit Tractor Supply Co
DSWNew
In stock
$109.99+ $7.95 shippingChecked 7 h ago
Visit DSW
Famous FootwearNew
In stock
$109.99+ $9.95 shippingChecked 7 h ago
Visit Famous Footwear
ShopSimonNew
Availability unknown
$79.98Checked 7 h ago
Visit ShopSimon
AmazonNew
Availability unknown
As an Amazon Associate, Deal.ai earns from qualifying purchases.
$79.99Free shippingChecked 7 h ago
Visit Amazon
LystNew
Availability unknown
$79.99Checked 7 h ago
Visit Lyst
BelkNew
Availability unknown
$88.00Checked 7 h ago
Visit Belk
Shoe CarnivalNew
Availability unknown
$109.99Checked 7 h ago
Visit Shoe Carnival
Jos. A. BankNew
Availability unknown
$110.00Checked 7 h ago
Visit Jos. A. Bank

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Eastland Ryan Leather Boot price history

Lowest price we've seen: $74.80 on Nov 15 at Kohl's. Tracked across 16 stores since Nov 15.

What reviewers say

Owners of Eastland's handsewn leather boots tend to praise the leather quality and out-of-the-box comfort, and the moc-toe styling draws compliments. Common complaints are that the soles wear down with heavy use and that the boots need breaking in.

What people mention

Leather qualityPraisedOwners say the leather is soft and develops a nice patina with wear.
ComfortPraisedThe padded insole and collar make them comfortable for long days on foot.
Break-inMixedSome find them stiff for the first week or two before they loosen up.
Sole durabilityCriticisedReviewers report the rubber sole wearing faster than expected with daily use.
TractionCriticisedOwners say grip is poor on wet pavement and ice.

About the Eastland Ryan Leather Boot

The Eastland Ryan is a men's leather ankle boot with a classic moc-toe silhouette. It has moc-toe stitching, a padded collar and a pull-on tab.

The boot closes with a lace-up system. It has a leather upper, a padded insole and a rubber sole.

Material: Leather upper, rubber sole
Closure: Lace-up
Toe style: Moc toe
Insole: Padded
Heel height: 1.125 in
Shaft height: 5 in
Boot circumference: 12 in
Features: Padded collar, pull-on tab, moc-toe stitching

Specifications

shoe_size: 10.5Source
color: OtherSource
Gore-Tex: NoSource
Outsole: RubberSource
Gender: MaleSource

Questions and answers

Is the Eastland Ryan good for everyday wear?: Yes. It is a casual leather ankle boot with a padded insole and a low heel, suited to daily wear with jeans or chinos. It is not built for heavy work or rough terrain.
Does the Ryan run true to size?: Eastland handsewn boots generally fit close to standard shoe size, and the leather loosens with wear. If you are between sizes or plan thick socks, consider going up half a size.
Is it waterproof?: No. The leather upper is not sealed against water, so it handles light damp but not rain or snow. Treat the leather and avoid deep puddles.
How does it compare with a taller moc-toe boot?: The Ryan is a low ankle boot, so it is lighter and easier to pair with casual outfits, but it gives less ankle support and coverage than a taller moc-toe boot.
What is the heel and shaft height?: The heel is about 1.125 inches and the shaft about 5 inches, with a boot circumference of roughly 12 inches. That makes it a low-profile ankle boot.
Can the sole be replaced?: The rubber sole is cemented rather than stitched, so a cobbler can usually resole it, though many owners simply replace the boots when the sole wears through.
Where is the Eastland Ryan Leather Boot cheapest?: At Kohl's, for $74.80, as of our latest check.
Where can I buy the Eastland Ryan Leather Boot?: 16 stores we checked sell it, including Shop Simon, Gilt, Famous Footwear, DSW, Tractor Supply Co.