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Eastland Cyrus Chelsea Boot

Eastland Cyrus Chelsea Boot

Best price now

$39.99at Macy'sObserved at 10:53 PM

50% under what the other stores charge

Compared across 7 stores. Prices are checked against each store and labelled with when.

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Our take on the Eastland Cyrus Chelsea Boot

The Eastland Cyrus is a men's pull-on Chelsea boot with a synthetic upper, fabric lining and a lugged polyurethane sole. It stands 5 1/2 inches at the shaft with a 1 1/2-inch heel, and the cushioned, shock-absorbing footbed is aimed at all-day comfort. At $39.99 at Macy's as of November 5, 2026, it sits at the low end of what the seven stores listing it charge.

Best forMen who want a slip-on boot for daily wearStanding or walking shifts where foot fatigue is a concernFall and winter casual outfitsShoppers after a budget Chelsea boot
Pros
  • Pull-on Chelsea design with no laces to tie
  • Cushioned, fully lined footbed for all-day wear
  • Shock-absorbing polyurethane sole
  • Lug outsole adds traction on slick ground
  • Ankle-high 5 1/2-inch shaft with a modest 1 1/2-inch heel
Cons
  • Synthetic upper and lining breathe less than leather
  • Polyurethane sole and upper won't age like leather
  • No safety toe or waterproofing claimed
  • Lug sole can pick up mud and snow

Eastland Cyrus Chelsea Boot prices at every store

  • Macy'sNew

    In stock

    $39.99Observed at 10:53 PM
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  • JCPenneyNew

    In stock

    $72.00Observed at 10:53 PM
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  • Famous FootwearNew

    In stock

    $79.99Observed at 10:53 PM
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  • Zappos.comNew

    In stock

    $84.99Observed at 10:53 PM
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  • ShopSimonNew

    Availability unknown

    $59.98Observed at 10:53 PM
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  • Rack Room ShoesNew

    Availability unknown

    $89.99Observed at 10:53 PM
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  • NordstromNew

    Availability unknown

    $90.00Observed at 10:53 PM
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Also available at

  • American Eagle OutfittersCheck price at American Eagle Outfitters
  • DSWCheck price at DSW
  • EastlandCheck price at Eastland

Eastland Cyrus Chelsea Boot price history

Lowest price we've seen: $39.99 on Nov 6 at Macy's. Tracked across 10 stores since Nov 6.

Specifications

Gender
Men's
Material
Polyurethane (outsole), Fabric (lining), Synthetic (upper)
Boot Style
Chelsea boot
Type
Boots
Closure Style
Pull-on
Heel Height
1 1/2"
Heel Height Measurement
1 1/2 inches
Safety Features
Shock-absorbing
Shaft Height
Ankle-high, 5 1/2 in
Age Group
Adult
Department
Men's
Solution For
Foot fatigue (all-day comfort)
Outsole Material
Polyurethane
Outsole Style
Lug sole
Sole Material
Polyurethane
Sole Support
Shock-absorbing
Sole Style
Lug sole
Traction Features
Traction
Footbed Features
Cushioned
Insole Features
Cushioned, Fully-lined
Lining Material
Fabric
Lining Type
Fully-lined
Pattern
Solid
Toe Style
Plain toe

Questions and answers

Is the Eastland Cyrus good for standing all day?
The cushioned, shock-absorbing footbed and polyurethane sole are built for comfort over long days on your feet. The synthetic upper and lining trap more heat than leather, so they suit cooler weather better.
Does it fit true to size?
It is a pull-on Chelsea with a fabric lining, so most men take their usual boot size. Try them on with the socks you plan to wear, since the ankle shaft is 5 1/2 inches.
Is it waterproof?
No. The upper is synthetic and the boot is not listed as waterproof, so it handles dry days and light damp better than rain or snow.
How does the Cyrus compare with a leather Chelsea boot?
It costs far less and needs no break-in care, but the synthetic upper and polyurethane sole won't mold to the foot or last as long as leather.
When is the best time to buy it?
At $39.99 at Macy's as of November 5, 2026, it is already near the bottom of its price range across the seven stores listing it. Boot discounts tend to deepen in late fall and after the holidays.
What is in the box?
One pair of boots. No extra laces or care products are included.
Where is the Eastland Cyrus Chelsea Boot cheapest?
At Macy's, for $39.99, 50% under what the other stores charge, as of our latest check.
Where can I buy the Eastland Cyrus Chelsea Boot?
10 stores we checked sell it, including Macy's, ShopSimon, JCPenney, Famous Footwear, Zappos.com.

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