• Cole Haan's sale section is full of editor-tested dress shoes with deals up to 62% off.
  • The biggest discount markdown is the Cole Haan ZERØGRAND Eon Wingtip Oxfords
    (62% off).
  • Deals include wingtips, loafers, dress sneakers, and boots.

CYBER MONDAY HAS ARRIVED, and I feel like I’ve trained for it the way marathoners prep for race day. This will be my fourth year covering the madness, and every season I’m reminded just how wild the deals can get—especially on footwear. I’ve tested hundreds of shoes in my time as a style editor, but Cole Haan is one of those brands I always circle on the calendar because its Cyber Monday sales are worth paying attention to.

SHOP COLE HAAN CYBER MONDAY SALE

If you’ve read Men’s Health style coverage before, you already know how much we love Cole Haan’s comfort tech. The brand makes some of the most comfortable dress shoes we’ve ever tested—like, “wear-them-all-day-and-forget-they’re-on” comfortable. I’ve worn its Oxfords to the office for back-to-back meetings, loafers out to dinner when I need to look put together, and dress sneakers for everything from art gallery openings to weekend brunches. They look sharp, they break in fast, and (unlike a lot of dress shoes) they don’t punish your feet for having a social life.

Best Runner-Up Deal
ZERØGRAND Eon Wingtip Oxfords
Cole Haan ZERØGRAND Eon Wingtip Oxfords
Now 62% Off
Best Deal
2.ZERØGRAND Laser Wingtip Oxfords
Cole Haan 2.ZERØGRAND Laser Wingtip Oxfords
Now 51% Off
Most Clean Silhouette
Grand Crosscourt Modern Perforated Sneaker
Cole Haan Grand Crosscourt Modern Perforated Sneaker
Now 48% Off
Best for Travelers
Grand Crosscourt Traveler Sneakers
Cole Haan Grand Crosscourt Traveler Sneakers
Now 35% Off
Best Wingtip
On Sale
Go-to Wingtip
Cole Haan Go-to Wingtip
Now 49% Off
Zerogrand Remastered Wingtip Oxfords
Cole Haan Zerogrand Remastered Wingtip Oxfords
Best Wingtip Oxford
2.ZERØGRAND Stitchlite Wingtip Oxfords
Cole Haan 2.ZERØGRAND Stitchlite Wingtip Oxfords
Now 43% Off
Best for Everyday
Grand Crosscourt Daily Laser Sneakers
Cole Haan Grand Crosscourt Daily Laser Sneakers
Now 39% Off
On Sale
Grandpro Angleace Sneakers
Cole Haan Grandpro Angleace Sneakers
Now 20% Off
Best Sneaker
On Sale
Grand Atlantic Sneaker
Cole Haan Grand Atlantic Sneaker
Now 37% Off
On Sale
Bedford Cap Toe Oxfords
Cole Haan Bedford Cap Toe Oxfords
Now 41% Off
Super Cushioned
ØriginalGrand Energyweave Stitchlite Wingtip Oxfords
Cole Haan ØriginalGrand Energyweave Stitchlite Wingtip Oxfords
Now 25% Off

This year, the standout deal is the ZERØGRAND Eon Wingtip Oxfords (62% off) which deliver a lightweight, flexible comfort but with a sportier vibe. It's perfect for office days when you're bouncing between meetings, work trips, and anytime you need dress-shoe polish without the stiffness. Another steal is the 2.ZERØGRAND Laser Wingtip Oxford, which is slashed a full 51% off—the biggest discount of the entire sale. It's incredibly versatile too: You can wear it with a tailored suit, a button-down and chinos, or even dark denim and a sweater to keep things elevated.

Then there's the Grand Crosscourt Traveler Sneakers (48% off), which is true everyday workhouse. It's clean, cushioned, and ridiculously wearable. Our editors have worn it everywhere: airport runs, coffee runs, country clubs, the list goes on.

There's no better time than Cyber Monday to upgrade your shoe rotation. The holiday crowd has already begun snatching up sizes, so you don't want to mess around and miss your opportunity.

SHOP COLE HAAN CYBER MONDAY SALE

Headshot of Joseph Cheatham
Joseph Cheatham
Style and Commerce Editor
As the Style and Commerce Editor for Men's Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.