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Deal.ai › Territory › Chelsea Boots
Territory
Territory Canyonlands Water-Resistant Chelsea Boot

Territory Canyonlands Water-Resistant 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.

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Our take on the Territory Canyonlands Water-Resistant Chelsea Boot

The Territory Canyonlands is a men's slip-on Chelsea boot in brown leather with a water-resistant, waterproof build, a foam insole and an EVA midsole on a rubber outsole. It is a budget-priced everyday boot rather than a dress boot. At $59.99 at ShopSimon as of November 8, 2026, it sits at the low end of what the four stores listing it new charge.

Best forShoppers who want a leather Chelsea boot under $60Wet-weather commuters and light outdoor wearSlip-on convenience for daily errandsBuyers who prefer a cushioned, lightweight sole
Pros
  • Genuine leather upper at a low price
  • Water-resistant and waterproof claims suit rain and slush
  • Slip-on Chelsea design with elastic side panels
  • Foam insole and EVA midsole keep it light and cushioned
  • Rubber outsole gives decent grip for the price
Cons
  • Waterproofing on budget leather often fades without care
  • EVA midsoles compress over time with heavy use
  • Slip-on fit can feel loose for narrow feet
  • Limited color choice in brown only

Territory Canyonlands Water-Resistant 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

    $69.99Observed at 7:08 AM
    Visit Walmart
  • TargetNew

    Out of stock

    $69.99Observed at 7:08 AM
    Visit Target

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

Territory Canyonlands Water-Resistant Chelsea Boot price history

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

Specifications

Size (US)
11.5Source
Fastening
Slip-OnSource
Color
BrownSource
Outsole
RubberSource
Age Group
AdultSource
Upper Material
LeatherSource
Midsole
EVASource
Insole
FoamSource

Questions and answers

Is the Canyonlands boot actually waterproof?
Territory lists it as both water-resistant and waterproof, with a leather upper and rubber outsole. Treat the leather periodically to keep rain out over time.
How does it fit compared with other Chelsea boots?
It is a slip-on with elastic side panels, so it fits like a standard Chelsea. Try your usual US size first; narrow feet may want a thicker sock.
Is $59.99 a good price for it?
It is the best new price among the four stores listing it as of November 8, 2026. That puts it at the low end of its current range.
What is the sole made of?
A rubber outsole over an EVA midsole, with a foam insole inside. That combination keeps the boot light but means the cushioning will compress with heavy daily wear.
Can I wear it in snow?
It handles wet sidewalks and light slush, but the EVA midsole and leather upper are not built for deep snow or long exposure to salt.
What comes in the box?
The pair of boots only. No extra laces or care products are included, so budget for a leather protector.
Where is the Territory Canyonlands Water-Resistant Chelsea Boot cheapest?
At ShopSimon, for $59.99, as of our latest check.
Where can I buy the Territory Canyonlands Water-Resistant Chelsea Boot?
4 stores we checked sell it, including Shop Simon, ShopSimon, Walmart, Target.

Stores we've priced the Territory Canyonlands Water-Resistant Chelsea Boot at

  • ShopSimon deals and prices
  • Target deals and prices
  • Walmart deals and prices

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