Black FridayDealsBuying guidesBrandsStoresResearchTermsPrivacydeal.ai apps
Black Friday 2026:TVsLaptopsHeadphonesAppleGamingVacuumsKitchenToysSmartwatchesTabletsFurnitureMattresses

© Deal.ai Inc.

AllTravelTechClothesShoesJewelryHomeBeautyOutdoorsToys
This hour's deals
St. John's Bay
St. John's Bay Men's Rutland Flat Heel Chelsea Boots
−68%
Shoes · JCPenney

Chelsea boots that go with everything you own

St. John's Bay Men's Rutland Flat Heel Chelsea Boots

St. John's Bay Rutland flat-heel Chelsea boots for easy everyday wear with jeans or chinos.

Deal score 7.6 · Steal
$31.99$100.00 JCPenney's regular price

You save $68.01 at JCPenney

Deal.ai's agents found this deal on November 6. The store may have changed its price since.

Why it's a great deal

  • JCPenney lists its regular price at $100.00: 68% off by its own figures
  • Rated 4.6 out of 5 by 24 buyers
Visit JCPenney

Every store we checked

  • JCPenneyNew

    In stock

    $31.99Observed at 7:08 AM
    Visit store
  • ModeSensNew

    In stock

    $48.00Observed at 7:08 AM
    Visit store
  • eBayPre-owned

    Availability unknownSold by crsartiques (100% positive, 1,200 ratings)Returns: Set by the eBay seller; the eBay Money Back Guarantee covers an item that doesn't arrive or isn't as described.

    $18.75+ $15.65 shippingVerified
    Visit store
  • eBayNew

    Availability unknownSold by brentannomyces (100% positive, 55 ratings)Returns: Set by the eBay seller; the eBay Money Back Guarantee covers an item that doesn't arrive or isn't as described.

    $29.00+ $8.71 shippingVerified
    Visit store
  • PoshmarkNew

    Availability unknown

    $41.00Observed at 7:08 AM
    Visit store
Price history and every store's price →

Reading JCPenney’s product page for the details…

Specs

Gender
Male, Men's
Boot Style
Chelsea Boots
Type
Boots
Closure Style
Pull On
Material
Polyester (14%), Polyurethene (86%), Thermoplastic-Rubber (100%) (sole)
Leather Material
Faux leather
Occasion
Cooler weather
Outsole Material
Thermoplastic-Rubber (100%)
Shaft Height
4 1/4 Inches
Age Group
Adult

About the St. John's Bay Men's Rutland Flat Heel Chelsea Boots

The St. John's Bay Rutland is a men's pull-on Chelsea boot in faux leather with a 4 1/4-inch shaft, a 3/4-inch flat heel and a thermoplastic-rubber sole. The memory foam cushioned footbed and elastic side gores make it an easy slip-on for cooler weather. It is a budget fashion boot, not a leather boot built to last years. It is rated 4.6 out of 5 from 24 ratings.

Best forMen who want a cheap Chelsea boot for fall and winter wearShoppers who prefer pull-on boots with no lacesCasual office and weekend outfitsBuyers who want cushioning without paying leather-boot prices
Pros
  • Memory foam footbed adds comfort for standing and walking
  • Pull-on Chelsea design with side gores is quick to put on
  • Flat 3/4-inch heel and round plain toe suit everyday wear
  • Thermoplastic-rubber outsole grips wet pavement better than smooth dress soles
  • Low price for a boot that looks like leather
Cons

More deals like this

  • All St. John's Bay deals and products
  • Early Black Friday Shoe Deals 2026

More from St. John's Bay

  • S
    St. John's Bay Kittery Lace Up Boots
    St. John's Bay Kittery Lace Up Boots
  • S
    St. John's Bay Lismore Strap Sandals
    St. John's Bay Lismore Strap Sandals
  • S
    St. John's Bay Bristol Flat Heel Chukka Boots

Ask our agent about this deal

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

Enter to send, Shift+Enter for a new line

  • Faux leather upper will crease, scuff and peel sooner than real leather
  • Polyester lining traps heat and moisture, so feet can get sweaty
  • Not waterproof; slush and salt will shorten its life
  • Little arch support for long days on hard floors
  • What reviewers say

    • 4.6 / 524 ratings

    With 24 ratings averaging 4.6 out of 5, owners mostly report a comfortable, good-looking boot for the money. Complaints center on the synthetic upper wearing quickly with heavy use.

    Pros
    • Comfortable out of the box thanks to the memory foam footbed
    • Easy to pull on and off
    • Looks dressier than its price
    Cons
    • Upper shows scuffs and creasing fast
    • Can feel warm and sweaty inside
    • Durability is limited with daily wear

    Questions and answers

    Is the Rutland Chelsea boot worth it?
    Yes if you want an inexpensive pull-on boot for casual fall and winter wear. Skip it if you need a boot that survives daily commuting or wet weather for years.
    Is it real leather?
    No. The upper is faux leather (about 86% polyurethane, 14% polyester) over a polyester and polyurethane lining. Expect it to crease and scuff more than genuine leather.
    How tall is the boot and how does it fit?
    The shaft is 4 1/4 inches with a 3/4-inch flat heel, so it sits at the ankle. It has a regular calf width and a round plain toe; most buyers take their usual size.
    Is it waterproof?
    No. The synthetic upper and lining resist light damp but not rain or slush. Treat it with a spray protector and avoid puddles and salt.
    What is in the box?
    One pair of boots. No shoe trees, polish or extra laces are included, and none are needed since the boot is laceless.
    When is it cheapest?
    St. John's Bay boots usually drop during fall and winter clearance and around major holiday sales. Watch the price history before buying at full price.
    St. John's Bay Bristol Flat Heel Chukka Boots
  • S
    St. John's Bay Men's Brock Block Heel Lace Up Boots
    St. John's Bay Men's Brock Block Heel Lace Up Boots
  • S
    St. John's Bay Dexterity Premium Stretch Men's Classic Fit Easy-on + Easy-off Adaptive Short Sleeve Polo Shirt
    St. John's Bay Dexterity Premium Stretch Men's Classic Fit Easy-on + Easy-off Adaptive Short Sleeve Polo Shirt
  • S
    St. John's Bay Women's Midweight Jacket
    St. John's Bay Women's Midweight Jacket
  • S
    St. John's Bay Women's Hamilton Flat Heel Riding Boots
    St. John's Bay Women's Hamilton Flat Heel Riding Boots
  • S
    St. John's Bay Tassie Stacked Heel Riding Boots
    St. John's Bay Tassie Stacked Heel Riding Boots