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Is Cole Haan Comfortable Again?

Dec 29, 2025

When I first moved to D.C. in 2005, Cole Haan shoes with Nike Air technology were all the rage. Costing several hundred dollars, they were the must-have Christmas gift for every intern and Staff Assistant I knew. The promise of pain free high heels (or at least less pain) seemed like a gift from above. But when Cole Haan ended its Nike partnership in 2012, the brand fell out of favor.

Last week, I noticed that Cole Haan was having a super sale and decided to give the brand another try. And ladies…I already posted to Instagram about this…but Cole Haan is back.

For myself, I purchased the Grand Ambition Angelina flats. The cushiony sole and internal support make them comfortable for every day wear. They also seem to have a bit more flex than other pointed flats. Plus, at $70 on sale, you’re not likely to find a better deal. I will, however, need to break them in.

I also bought the Grand Ambition tall boot. They’re a really nice boot — well-made, comfortable, nice leather. My only complaint is that you need to wear thin socks. Thick socks make them too tight. It’s a minor issue, and at $140, there isn’t a better deal on the market.

They also make this style in a high heel option (pictured) and an ankle boot. I haven’t tried these, but if they’re as comfortable as the flats and tall boots, they’re worth a try.

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  1. s-p-c says:

    Love hearing this! Through the magic of a great shoe-repair place and the rotation of multiple pairs bought on eBay/Poshmark that live at the office, I am wearing Cole Haan wedges with Nike Air technology to this day. Glad to know the brand is back for when my old pairs finally bite the dust.

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