WHEN IT COMES to dress shoes, I have very little patience for pairs that look great at 9 a.m. and feel terrible by 3 p.m. I don’t have that problem with Cole Haan because the brand makes the most comfortable dress shoes (and dress sneakers). I can wear them anywhere whether I’m commuting into the office, bouncing between meetings, or heading straight to dinner afterward. And during Prime Day, some of my favorite styles are finally seeing worthwhile discounts up to 61% off.
SHOP PRIME DAY COLE HAAN DEALS
I’ve spent plenty of time in the ZerøGrand Stitchlite Oxford, which remains one of the most comfortable pairs I own. The lightweight knit upper feels more like a performance sneaker than a traditional leather oxford, while the cushioned sole keeps my feet happy during long days on the move. When I need something that can handle casual meetings and long travel days alike, I slip on the Grand Crosscourt Traveler Sneaker. This tennis shoe silhouette is clean, versatile, and easy to style with a bunch of relaxed fits. Inside, there’s a proprietary Grandfoam technology that feels soft and spongy without sinking into the ground with every step.
Another one of my recommendations that’s on the sale is the GrandPro Breakaway Sneaker. The soccer-inspired model blends leather and suede overlays for its upper, while the rubber sole has the same lightweight comfort as my favorite pair of Nikes. I wear this pair to the park or bar for drinks, but also rock it for laid-back days at the office.
What I love most about Cole Haan shoes is the cushioning is plush without feeling bulky, the materials are lightweight and flexible, and none of them require the dreaded break-in period. If you’ve been waiting to upgrade your office-ready footwear rotation or want shoes that can pull double duty from work to dinner, Prime Day is one of the best times of the year to do it. Plus, this is the only Prime Day sale happening this summer, so I would really take advantage of this opportunity.
Best Cole Haan Deals
SHOP PRIME DAY COLE HAAN DEALS
As the Style and Reviews 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.

