Black FridayDealsBuying guidesBrandsStoresResearchTermsPrivacydeal.ai apps
Black Friday 2026:TVsLaptopsHeadphonesAppleGamingVacuumsKitchenToysSmartwatchesTabletsFurnitureMattresses

© Deal.ai Inc.

AllTravelTechClothesShoesJewelryHomeBeautyOutdoorsToys
This hour's deals
Kenneth Cole Reaction
Kenneth Cole Reaction Leland Cap Toe Two Buckle Monk Shoe
−50%
Shoes · Macy's

Double-buckle monk shoes for the guy who dresses sharp

Kenneth Cole Reaction Leland Cap Toe Two Buckle Monk Shoe

Kenneth Cole Reaction Leland cap-toe monk shoes with two buckles, for anyone who wants a dressy shoe with a little personality.

Deal score 6.1 · Great deal
$54.50$109.00 Macy's regular price

You save $54.50 at Macy's

This deal was in an earlier drop. The store may have changed its price since.

Why it's a great deal

  • Elsewhere right now: Belk $76.30, Zappos.com $108.95, DSW $108.99 (typical $108.95 across 3 stores)
  • Cheaper than all 3 other stores selling it right now
  • Macy's lists its regular price at $109.00: 50% off by its own figures
Visit Macy's

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

Every store we checked

  • Macy'sNew

    In stock

    $54.50Observed at 10:08 PM
    Visit store
  • BelkNew

    In stock

    $76.30Observed at 10:08 PM
    Visit store
  • Zappos.comNew

    In stock

    $108.95Observed at 10:08 PM
    Visit store
  • ModeSensNew

    Availability unknown

    $77.00Observed at 10:08 PM
    Visit store
Price history and every store's price →

Reading Macy's’s product page for the details…

Specs

Width
Width Medium
Department
Men's
Material
Faux Leather, Rubber
Closure Style
Lace-up, Buckle
Style
Formal
With Arch Support
Yes
Lining Material
Leather
Support Type
Cushioning
Outsole Material
Rubber Outsole
Toe Style
Cap Toe

About the Kenneth Cole Reaction Leland Cap Toe Two Buckle Monk Shoe

The Kenneth Cole Reaction Leland is a men's double-monk dress shoe with a cap toe, a faux-leather upper and a rubber outsole. It pairs a buckle closure with lacing, and the leather lining and cushioned footbed with arch support are aimed at all-day wear. At $54.50 at Macy's as of November 5, 2026, it sits at the low end of what this shoe has sold for recently, well under its usual list pricing.

Best forMen who need an affordable dress shoe for work or eventsShoppers who want the monk-strap look without paying designer pricesWearers who want arch support in a formal shoeOccasional wear at weddings, interviews and office days
Pros
  • Double-monk buckle styling reads dressier than a plain lace-up
  • Cushioned footbed with arch support adds comfort for a formal shoe
  • Leather lining is a step up from the synthetic upper
  • Rubber outsole grips better and wears longer than leather soles
  • Low price for a cap-toe dress shoe
Cons

More deals like this

  • All Kenneth Cole Reaction deals and products
  • Early Black Friday Shoe Deals 2026

More from Kenneth Cole Reaction

  • K
    Kenneth Cole Reaction KC1373 Women's Sunglasses
    Kenneth Cole Reaction KC1373 Women's Sunglasses
  • K
    Kenneth Cole Reaction Renegade Expandable Spinner
    Kenneth Cole Reaction Renegade Expandable Spinner
  • K
    Kenneth Cole Reaction Men's Suit
  • Upper is faux leather, so it will not crease or age like real leather
  • Buckles and lacing together can make it fussy to put on
  • Rubber sole looks less refined than leather at formal events
  • Synthetic upper may run warm and less breathable than full leather

What reviewers say

Owner feedback on the Leland is limited, but buyers of Kenneth Cole Reaction dress shoes generally treat them as budget formal shoes that look sharper than their price. Common notes are a comfortable cushioned footbed and a stiff break-in period.

What people mention
  • ComfortPraisedOwners say the cushioned footbed and arch support make these wearable through a full workday.
  • MaterialMixedThe faux-leather upper looks the part but feels stiffer and less breathable than real leather.
  • FitMixedSome wearers find the medium width snug and suggest sizing up or breaking them in.
  • BucklesMixedThe double-monk straps draw compliments but take extra time to fasten and adjust.
  • Break-inCriticisedSeveral buyers report a stiff first few wears before the shoe softens.

Questions and answers

Is $54.50 a good price for the Leland monk shoe?
Yes. That is the lowest new price among the four stores listing it as of November 5, 2026, and it is well below typical list pricing for a cap-toe dress shoe.
Is the upper real leather?
No. The upper is faux leather, though the lining is leather and the outsole is rubber.
How does the Leland fit?
It comes in medium width and buyers often describe it as running slightly narrow, so consider sizing up if you are between sizes.
Can I wear these every day?
They work for regular office wear thanks to the cushioned footbed and rubber outsole, but the synthetic upper will show wear sooner than real leather.
What is the difference between the Leland and a plain cap-toe oxford?
The Leland adds double-monk buckles on top of lacing, giving a dressier look, while a plain cap-toe oxford is simpler and faster to put on.
Kenneth Cole Reaction Men's Suit
  • K
    Kenneth Cole Reaction Men's Ready Flex Slim Fit Suit
    Kenneth Cole Reaction Men's Ready Flex Slim Fit Suit
  • K
    Kenneth Cole Reaction Salinda Women's Boots
    Kenneth Cole Reaction Salinda Women's Boots
  • K
    Kenneth Cole Reaction Captain Combat Men's Boot
    Kenneth Cole Reaction Captain Combat Men's Boot
  • K
    Kenneth Cole Reaction Men's Flex Suit Jacket
    Kenneth Cole Reaction Men's Flex Suit Jacket
  • K
    Kenneth Cole Reaction Men's Reversible Plaque Buckle Belt
    Kenneth Cole Reaction Men's Reversible Plaque Buckle Belt