Is the Eastland Daily Double waterproof?

It is listed as waterproof, but it has no Gore-Tex membrane. The smooth leather resists light rain; standing water can still get in through the side gores and stitching.

How does the sizing run?

It comes in US sizes 4 to 14 in D width only. Owners often say it fits true to size but snug, so wide feet may want to size up.

What is the heel and shaft height?

The block heel is about 1 3/8 inches and the shaft is 5 inches, so it sits at the ankle.

Is $69.95 a good price?

That is the best new price across 6 stores as of November 7, 2026, at eBay. Chelsea boots from Eastland typically sell in the $70 to $120 range, so this sits at the low end.

Can the insole be replaced?

The Active Memory Foam insole is removable in most pairs, so you can swap in your own orthotic if the foam flattens.

Where can I buy the Eastland Daily Double Men's Leather Chelsea Boots?

8 stores we checked sell it, including Walmart, Shop Simon, Gilt, JCPenney, Zappos.

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Eastland Daily Double Men's Leather Chelsea Boots

Best price now

$79.99at WalmartObserved at 8:33 AM

Compared across 5 stores. Prices are checked against each store and labelled with when.

Visit Walmart

Eastland Daily Double Men's Leather Chelsea Boots

Best price now

$79.99at WalmartObserved at 8:33 AM

Compared across 5 stores. Prices are checked against each store and labelled with when.

Visit Walmart

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Our take on the Eastland Daily Double Men's Leather Chelsea Boots

The Eastland Daily Double is a men's slip-on Chelsea boot in smooth leather with twin side gores, a 5-inch shaft and a 1 3/8-inch block heel. It uses Eastland's Active Memory Foam insole over a foam, polyurethane and cork footbed, and a TPR outsole for flex and slip resistance. The best new price is $69.95 at eBay as of November 7, 2026, with 6 stores selling it new.

Best forMen who want a pull-on boot for office and casual wearShoppers who prefer a cushioned insole over a hard leather footbedWearers who need a low block heel rather than a flat sole

Pros

Slip-on Chelsea design with side gores, no laces to tie
Memory foam insole conforms to the foot for all-day cushioning
Smooth leather upper is easy to wipe clean
TPR outsole is flexible and slip resistant
Moderate 5-inch shaft and 1 3/8-inch heel suit everyday wear

Cons

Not Gore-Tex, so wet-weather protection depends on the leather finish
Textile lining and foam insole can wear faster than leather
Only D width offered; wide or narrow feet may not fit
Smooth leather scuffs and needs regular care

Eastland Daily Double Men's Leather Chelsea Boots prices at every store

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 shippingObserved at 8:33 AM
Visit Walmart
Shop SimonNew
In stock
$79.98+ $4.95 shippingObserved at 8:17 AM
Visit Shop Simon
GiltNew
In stock
$79.99+ $11.99 shippingObserved at 8:17 AM
Visit Gilt
JCPenneyNew
In stock
$100.00Free shippingObserved at 8:17 AM
Visit JCPenney
ZapposNew
In stock
$119.99Free shippingObserved at 8:17 AM
Visit Zappos

Also available at

DSWCheck price at DSW
eBayCheck price at eBay
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Eastland Daily Double Men's Leather Chelsea Boots price history

Lowest price we've seen: $79.98 on Nov 7 at Shop Simon. Tracked across 6 stores since Nov 7.

What reviewers say

Owners of Eastland memory-foam boots generally report easy break-in and comfortable cushioning for standing and walking. Common complaints center on the foam insole flattening over time and the leather showing scuffs.

What people mention

ComfortPraisedOwners say the memory foam insole feels soft and supportive from the first wear.
Break-inPraisedReviewers report the leather softens quickly with little rubbing.
Insole durabilityCriticisedSome owners say the foam flattens and loses cushioning after months of use.
Leather careMixedThe smooth leather is easy to clean but scuffs and shows marks without regular polishing.
FitMixedThe D width fits many buyers well, but some find it snug across the instep.

About the Eastland Daily Double Men's Leather Chelsea Boots

At the office or kicking back, our Daily Double packs comfort and authentic style right out of the box. Easy to care for smooth leather upper. Eastland Exclusive Active Memory Foam comfort insole supports and conforms to the curves of your foot. TPR outsole for great flexibility, slip resistance, insulation and durability. Boot Height: 5". Heel Height: 1 3-8".

Specifications

shoe_size: 10.5 D(M) USSource
clothing_size: 10.5Source
color: BrownSource
size: 10.5Source
Gore-Tex: NoSource

Questions and answers

Is the Eastland Daily Double waterproof?: It is listed as waterproof, but it has no Gore-Tex membrane. The smooth leather resists light rain; standing water can still get in through the side gores and stitching.
How does the sizing run?: It comes in US sizes 4 to 14 in D width only. Owners often say it fits true to size but snug, so wide feet may want to size up.
What is the heel and shaft height?: The block heel is about 1 3/8 inches and the shaft is 5 inches, so it sits at the ankle.
Is $69.95 a good price?: That is the best new price across 6 stores as of November 7, 2026, at eBay. Chelsea boots from Eastland typically sell in the $70 to $120 range, so this sits at the low end.
Can the insole be replaced?: The Active Memory Foam insole is removable in most pairs, so you can swap in your own orthotic if the foam flattens.
Where is the Eastland Daily Double Men's Leather Chelsea Boots cheapest?: At Walmart, for $79.99, as of our latest check.
Where can I buy the Eastland Daily Double Men's Leather Chelsea Boots?: 8 stores we checked sell it, including Walmart, Shop Simon, Gilt, JCPenney, Zappos.