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The Glycerin StealthFit 22 hits the sweet spot between softness, structure, and style. It tops a plush, cloud-like sole with a stretchy, sock-like upper, for a shoe that hugs in all the right places.

My foot issues are plentiful—from recurring plantar fasciitis to wobbling ankles to having a non-standard width—so finding the best walking shoe to fit my needs can be a challenge. In the name of ...