Is $92.50 a good price for the Kenneth Cole Raymond?

It is the best new price among the 6 stores listing it as of November 5, 2026. Check the price history on this page to see how it compares with earlier lows.

Does the Raymond have arch support?

Yes. The cushioned footbed has built-in arch support and is removable, so you can swap in your own insole.

How do the Raymond Chelsea boots fit?

They are pull-on boots with elastic gore panels and no laces, so fit depends on your usual size. Try them on with the socks you plan to wear.

What is the upper made of?

The upper is Balboa leather with a smooth finish. Wipe it clean with a damp cloth and avoid soaking it.

Can I wear the Raymond to the office?

Yes. The almond toe and smooth leather make it a smart-casual boot that works with trousers and chinos.

What comes in the box?

One pair of boots with the removable cushioned footbed inserted. No shoe trees or care kit are included.

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This hour's deals

Kenneth Cole Raymond Men's Casual Slip-On Boot

−50%

Shoes · Macy's

Slip on and go in Kenneth Cole leather

Name: Kenneth Cole Raymond Men's Casual Slip-On Boot
Brand: Kenneth Cole
Rating: 2.8 (5 reviews)

Kenneth Cole Raymond Men's Casual Slip-On Boot

A casual slip-on boot from Kenneth Cole for guys who want easy leather style without laces.

Deal score 6.1 · Great deal

$92.50$185.00 Macy's regular price

You save $92.50 at Macy's

Deal.ai's agents found this deal on November 5. The store may have changed its price since.

Why it's a great deal

Elsewhere right now: Zappos.com $157.20, DSW $184.99, Kenneth Cole $185.00, and 2 more (typical $185.00 across 5 stores)
Cheaper than all 5 other stores selling it right now
Macy's lists its regular price at $185.00: 50% off by its own figures

Visit Macy's

Every store we checked

Macy'sNew
In stock
$92.50Observed at 8:58 PM
Visit store
Zappos.comNew
In stock
$157.20Observed at 8:58 PM
Visit store
NordstromNew
In stock
$185.00Observed at 8:58 PM
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ModeSensNew
Availability unknown
$158.00Observed at 8:58 PM
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BelkNew
Availability unknown
$185.00Observed at 8:58 PM
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eBayNew
Availability unknownSold by soledistrict_supply
$212.88Observed at 8:58 PM
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Price history and every store's price →

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

Specs

Gender: Men's
Boot Style: Chelsea boots
Type: Boot
Closure Style: Pull-on
Material: Rubber/synthetic (sole), Leather (upper)
Leather Material: Balboa leather
Outsole Material: Rubber/synthetic
Sole Material: Rubber/synthetic
Department: Men's
Toe Shape: Almond-shaped

About the Kenneth Cole Raymond Men's Casual Slip-On Boot

The Kenneth Cole Raymond is a men's Chelsea boot in smooth Balboa leather with elastic gore panels and a pull tab for easy on and off. It has a removable cushioned footbed with built-in arch support and a flexible rubber sole. The best new price is $92.50 at Macy's as of November 5, 2026, with 6 stores listing it new.

Best forMen who want a dress-casual Chelsea bootWearers who need arch support in a slip-onOffice and smart-casual outfitsAnyone who wants a removable footbed

Pros

Slip-on Chelsea design with elastic gore panels
Balboa leather upper wipes clean
Removable cushioned footbed with arch support
Flexible rubber sole for easy walking
Almond toe keeps it dressy enough for work

Cons

Leather upper needs wiping and care to stay smooth

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