Thursday, March 5
  • Amazon officially announced the dates for its fall Prime Day, Prime Big Deal Days.
  • The two-day savings event will take place from October 7 and run through midnight, October 8.
  • We’re already seeing savings on editor-tested products from Apple, Yeti, Brooks, Garmin, and more.

AMAZON PRIME DAY is back and better than ever, especially when it comes to footwear. Cole Haan, in particular, is seeing some of the biggest markdowns. We’re talking versatile leather dress sneakers, sharp loafers, everyday business casual shoes, and classic oxfords that actually look and feel good. As a style editor who’s been covering Prime Day for years, I know not every discount is worth your money, but Cole Haan consistently delivers on comfort, durability, and style.

I’ve scrolled through endless Prime Day sales of dress shoes, I can tell you most deals don’t really move the needle. But when I saw Cole Haan models marked down, I perked up fast—because these are the rare discounts that check both boxes: Polished enough for the office, comfortable enough for commuting, and cool enough for weekends. Some brands offer stiff soles or outdated silhouettes, but Cole Haan nails that balance of work-ready polish and all-day wearability. And now is the time to grab a pair at these superb savings.

SHOP COLE HAAN PRIME DAY DEALS

Best Lightweight

2.0 Zerogrand Stitchlite Oxford

Cole Haan 2.0 Zerogrand Stitchlite Oxford

Now 52% Off

Best Everyday Work Shoe

Cole Haan Originalgrand Remastered Stitchlite Oxfords

Now 19% Off

Most Comfortable

Cole Haan Zerogrand Wing Oxford

Now 17% Off

Best Minimal Sneaker

Cole Haan Grand Crosscourt Premier Sneaker

Now 42% Off

Best Breathable

Cole Haan Grand Crosscourt Modern Perforated Sneaker

Now 36% Off

Best Retro-Inspired Dress Sneaker

Cole Haan Grand Atlantic Oxford

Now 57% Off

Best Travel Shoe

Cole Haan Grand Crosscourt Traveler Sneaker

Now 41% Off

Best Sport-Luxe Sneaker

Cole Haan Grand Atlantic Sneaker

Now 47% Off

Best Weekend Sneaker

Cole Haan Grandpro Breakaway Sneaker

Now 25% Off

Best OG Style

Cole Haan Pinch Tassel Loafer

Now 27% Off

Best for Formal Occasions

Cole Haan Bedford Cap Toe Oxfords

Now 12% Off

The Most Classic

Cole Haan Bedford Wingtip Oxford

Now 17% Off

Prime Day is the perfect excuse to step up your footwear game, and Cole Haan has three standout picks on sale worth adding to your cart. For starters, the Zerogrand Wing Oxford is a classic silhouette that looks great in multiple settings including the office, dinners, or nights out. I’ve worn mine sprinting between meetings, and never felt the drag of my long schedule. The Grand Crosscourt Traveler Sneaker blends lightweight cushioning with a clean design, so you can rock it from city sightseeing to casual Fridays. It’s so polished taht some of our editors even sport it to the country club. And the Pinch Tassel Loafer is that business-casual staple that looks just as good with tailored slacks as it does with shorts, and yes—you can absolutely style it with socks for a unique twist.

Whether you need an office-ready loafer, a sneaker you can dress up, or a dress shoe that won’t wreck your feet after a long day, these are the Prime Day (October 7-8) deals that actually upgrade your wardrobe for the long haul.

SHOP COLE HAAN PRIME DAY DEALS

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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.

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