Best Cyber Monday Men’s Shoe and Boot Deals 2025

Cyber Monday is here. While some sales are generally a continuation of Black Friday, many retailers are adding new markdowns into the mix. Whether you’re a sneaker collector, someone revamping their work wardrobe, or just generally looking for a new pair of shoes, Cyber Monday is the last chance to get deep discounts.

Cyber Monday is well underway, and while many sales are generally a continuation of Black Friday, many retailers are adding new markdowns to today’s deals.

Some of our favorite men’s shoes and boots brands are running huge sitewide sales. Greats has a nice range of its shoes, including bestselling sneakers, on sale for up to 60% off. If you prefer bigger retailers, sportswear brands like Adidas and Nike are also offering sales with huge discounts, including some of their most popular styles.

Even boot and dress shoe brands like Fluevog, Timberland, and Grant Stone (which makes one of the best loafers) are offering some great deals.Big box stores like Macy’s are also good places to shop variety of brands, like Cole Haan and Rockport, with deep discounts up to 60% off on some selections.

Browse today’s full lineup of sales across all categories in our roundup of the best Cyber Monday deals.

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Best Cyber Monday shoes and boots deals

Adidas: Expect savings up to 60% off select styles and discounts on fan favorites like Sambas.
Allbirds: Save up to 50% on select styles
Allen Edmonds: The storied brand is offering some classic styles at more than 30% off.
Alohas: Save up to 40% off select styles of their men’s sneakers
Bespoke Unit: You’ll find brands like Danner, Vasque, and Seavees on sale for as much as 50% off.
Bootbarn: If you’re looking for Western boots, you’ll find select styles from brands like Justin, Ariat, and Dan Post for as much as 50% off.
Beckett Simonon: Right now at this DTC brand that we love you can get any of their boots for $199, a savings of more than 25%.
Bruno Marc: Up to 33% off select styles, from sneakers to Chelsea boots.
Clarks: Save up to 60% with the promo code STEALS
Cole Haan: Save up to 60% sitewide
DSW: Take 30% off storewide
Florsheim: Dec. 2, you get 30% sitewide, plus free shipping and easy returns with code CMF5.
G. H. Bass: Get select styles of Weejuns, including bit loafers, for more than 40% off.
Fluevog: This luxury brand is offering more than 30% on select styles along with free returns on domestic orders.
Grant Stone: Save 20% when you spend $450 or more, plus find select boots at up to 40% off.
Greats: The brand is offering 30% to 60% off, including on its best-selling Royale 2.0 and its Corso Drivers.
Hoka: $40 off $200, $50 off $250, and $60 off $300+
Nike: Save up to 50%, plus an extra 25% with the code BFRIDAY
Rothy’s: Save 30% sitewide
Sierra: Save up to 75% on shoes sitewide
Timberland: Save 30% sitewide
UGG: Save up to 50% on select shoes

The best Cyber Monday shoes and boots deals

Ranging from sneakers to dress shoes, this year’s Cyber Monday deals cover every style you could possibly need (or want). Whether you’re interested in a new casual style or a pair of the best dress shoes for men, you’ll find deep discounts on top brands.

Air Jordan 1

Nike Air Jordan 1 High OG

It’s hard to think of a more iconic style than the Air Jordan 1. Originally released in 1985, these basketball shoes have long been a fan favorite.

allbirds tree breezer beige

Allbirds Men’s Tree Runners

A thoughtfully crafted shoe that’s light and breezy. It offers comfort and is ideal for every escapade with its cooling design.

Nike Dunk

Nike Dunk Low Retro

These are another of the brand’s old-school offerings equally beloved by skaters and fashion trendsetters. They feature durable higher quality suede and leather uppers and a silhouette guaranteed to elevate your everyday style.

Air Jordan 12

Nike Air Jordan 12

Worn by Michael Jordan during the 1996-1997 season, this silhouette has seen championship-winning greatness.

Nike Pegasus Trail 5

The Nike Pegasus Trail 5 are versatile shoes that provide a smooth ride, whether running on trails or pavement.

Men's Chukka Lug

UGG Men’s Chukka Lug

These chukka boots bring all the UGG comfort to the classic chukka boot. Wear them on days when you need something nicer than a slipper, but still just as comfortable.

Allbirds Wool Runner

Allbirds Men’s Wool Runners

Allbirds Men’s Wool Runners sneakers are super comfortable, lightweight, and stylish. Since officially launching in 2016, San Francisco-based startup Allbirds now makes six different shoe silhouettes and has experimented with a variety of sustainable materials.

Men's Neumel

UGG Men’s Neumel

For something a little more elevated, go for this chukka style boot. The boots are lined with UGGplush wool and have a durable sole that makes them perfect for outdoor activities.

Sneaker

Allbirds Runner NZ Remix

sneaker

Cole Haan ZERØGRAND Remastered Wingtip Oxfords

Florsheim

Timberland 3-eye

Moral Code

Cyber Monday men’s shoes and boots deals FAQs

What are the best Cyber Monday men’s shoe deals?

It all comes down to what you’re looking for. Adidas and Nike have the biggest discounts of the year on sneakers, while Cole Haan has many great deals on dress shoes. Macy’s also has deep discounts on a range of brands and styles.

Should I shop for shoes during Cyber Monday?

Yes. Whether you’re shopping for holiday gifts, new workout shoes, or warm shoes for the winter season, this will be your last chance to save on a large variety of brands. While many of the brands included offer sales periodically throughout the year, Cyber Monday typically features the deepest discounts.

Shopping for more discounts? Check out all of our Cyber Monday coverage.

Andrew Amelinckx

Freelance Reporter, Insider Reviews

You can purchase logo and accolade licensing to this story here.

Disclosure: Written and researched by the Insider Reviews team. We highlight products and services you might find interesting. If you buy them, we may get a small share of the revenue from the sale from our partners. We may receive products free of charge from manufacturers to test. This does not drive our decision as to whether or not a product is featured or recommended. We operate independently from our advertising team. We welcome your feedback. Email us at [email protected].

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