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Cole Haan makes some of the most popular sneakers, dress shoes, and sneaker-dress shoe hybrids around, but to sleep on the brand’s wide variety of boots would be a mistake. Many integrate the comfort-focused tech that the brand is known for, including a pair of chukka boots that’s currently on sale at Macy’s with a substantial discount.
The Cole Haan Men’s Grand Aerion Leather Lace-Up Chukka Boot is on sale for $131 at Macy’s, 41% off its normal $220 price tag. It comes in whole and half sizes from 7 to 13 and three different colors: black, Irish Coffee, and British Tan, all of which are currently available in all sizes, albeit some with low stock.
Cole Haan Men’s Grand Aerion Leather Lace-Up Chukka Boot, $131 (was $220) at Macy’s

The boots have a very traditional round toe, lace-up chukka silhouette, and a leather upper with a lovely sheen in all three colors. Cole Haan really nailed the small details, like blind eyelets and tonal stitching, for a sleek, classic look. The footbed and outsole are quite untraditional, as both are made of EVA, a synthetic material that’s lightweight, shock-absorbing, flexible, and water-resistant, properties that make it very commonly used in athletic footwear. It’s this combination of old and new that’s at the heart of these boots and so much of what Cole Haan makes.
Related: Cole Haan’s Stylish Water-Resistant Chelsea Boots Are Nearly 50% Off at Nordstrom Rack
Deals We’re Loving
- Johnston & Murphy Men’s Boswell Chukka Boots, $88 (was $175) at Macy’s
- Johnston & Murphy Men’s XC+ Parker Chukka Round Toe Boots, $132 (was $189) at Macy’s
- Cole Haan Men’s Grand Neoclassic Flexcraft Chukka Boots, $154 (was $220) at Macy’s
The Cole Haan Men’s Grand Aerion Leather Lace-Up Chukka Boot is a very comfortable, very attractive pair of chukka boots that’s on sale for $131 smack dab in the middle of chukka boot season. Do yourself a favor and add a pair to your wardrobe. You’ll get plenty of compliments, and your feet will thank you.