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This hour's deals
Dockers
Dockers Men's Brookside Chelsea Boot
−53%
Shoes · ShopSimon

Dockers Men's Brookside Chelsea Boot

Deal score 5.4 · Good deal
$39.98$85.00 ShopSimon's regular price

You save $45.02 at ShopSimon

Deal.ai's agents found this deal on November 11. The store may have changed its price since.

Why it's a great deal

  • Elsewhere right now: Target $39.98, Walmart $39.98, Zappos.com $42.50, and 2 more (typical $42.50 across 5 stores)
  • ShopSimon lists its regular price at $85.00: 53% off by its own figures
Visit ShopSimon

Every store we checked

  • ShopSimonNew

    In stock

    $39.98Checked 53 min ago
    Visit ShopSimon
  • TargetNew

    In stock

    $39.98Checked 53 min ago
    Visit Target
  • Nashville Shoe WarehouseNew

    In stock

    $39.98Checked 53 min ago
    Visit Nashville Shoe Warehouse
  • eBayNew

    In stockSold by nashvilleshoewarehouse

    $39.98Checked 53 min ago
    Visit eBay
  • WalmartNew

    In stockSold by Nashville Shoe Warehouse

    $39.98Checked 53 min ago
    Visit Walmart
  • Zappos.comNew

    In stock

    $42.50Checked 53 min ago
    Visit Zappos.com
  • Macy'sNew

    In stock

    $42.50Checked 53 min ago
    Visit Macy's
  • Shop SimonNew

    In stock

    $39.98+ $4.95 shippingChecked 53 min ago
    Visit Shop Simon
  • Kohl'sNew

    In stock

    $72.25Checked 53 min ago
    Visit Kohl's
  • eBayPre-owned

    Out of stockSold by gegalou

    $29.99Checked 53 min ago
    Visit eBay

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

Price history and every store's price →

Reading ShopSimon’s product page for the details…

Specs

Gore-Tex
NoSource
Fastening
Slip-OnSource
Color
BlackSource
Outsole
TPRSource
Age Group
AdultSource
Lining
Microfiber, TextileSource
Gender
MaleSource
Upper Material
SyntheticSource
Insole
EVA, FoamSource

About the Dockers Men's Brookside Chelsea Boot

The Dockers Brookside is a men's slip-on Chelsea boot with a synthetic upper, elastic side gores and pull tabs for easy entry. A foam and EVA insole cushions the foot, and a TPR outsole handles pavement and light rain. It is a budget-leaning dress-casual boot that suits office days and weekend wear. Against leather Chelseas from Clarks or Blundstone it trades durability for a lighter, easier-care build.

Best forMen who want a slip-on boot for office or smart-casual wearShoppers after an easy-care synthetic bootEveryday commuters who want quick on and offWet-weather city walking on a budget
Pros
  • Slip-on Chelsea design with elastic gores and pull tabs
  • Foam and EVA insole adds step-in cushioning
  • TPR outsole grips pavement and sheds light rain
  • Synthetic upper wipes clean and needs no polishing
  • Lighter than most leather Chelsea boots
Cons

More deals like this

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Price facts

  • This deal was $39.98 at ShopSimon on Nov 11.
  • Lowest price today: $39.98 at ShopSimon (checked Nov 11, 2026).
  • Checked at 9 stores.

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Synthetic upper will not age or crease like leather
  • TPR outsole is less durable than rubber or leather soles
  • Not waterproof; no Gore-Tex membrane
  • Limited arch support for long days on feet
  • What reviewers say

    Owners of budget Chelsea boots in this class generally like the easy slip-on fit and light weight. Common complaints center on the synthetic upper looking less refined than leather and the outsole wearing faster than expected.

    What people mention
    • Upper materialMixedOwners say the synthetic upper is easy to clean but looks less premium than leather.
    • Outsole wearCriticisedSome report the TPR outsole wearing faster than rubber or leather soles under daily use.
    • ComfortPraisedThe foam and EVA insole is called comfortable straight out of the box.
    • Slip-on fitPraisedElastic gores and pull tabs make the boot quick to put on and take off.
    • SupportCriticisedLong days on feet draw complaints about thin arch support.

    Questions and answers

    Is the Brookside Chelsea boot waterproof?
    No. It has no Gore-Tex membrane and a synthetic upper, so it handles light rain but not puddles or sustained wet weather.
    How does it fit compared with other Chelsea boots?
    It runs true to standard US men's sizing. The elastic gores give some stretch, so a wide foot can usually stay with its normal size.
    Is it good for standing all day?
    The foam and EVA insole cushions at first, but arch support is modest. Men who stand for hours often add an aftermarket insole.
    Can it be worn with a suit?
    It works for business casual and smart-casual outfits. The synthetic upper is less dressy than a leather Chelsea, so it is a stretch with formal suits.
    How do I care for the synthetic upper?
    Wipe it with a damp cloth and mild soap, then air dry away from direct heat. No polish or conditioner is needed.
    What is in the box?
    One pair of boots. No shoe trees, bags or extra laces are included.

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