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I don't have your height or ankle concerns, but I have special shoe needs due to my Morton's toe and previous foot surgeries so I'm always looking for comfortable shoes. Granted what is comfortable for one may not be for another, as I have experienced, so try everything on, even if it isn't labeled "comfort" or may look like it won't work.
Consistently I've found Sofft brand shoes to be pretty comfortable, and moderately priced ($100 or below when not on sale), and not only are they sold at Macy's and Nordstrom, but even in my cow town. Cole Haan is nice but costs more, and my favorite is Anyi Lu which I only get at a massive Nordstrom sale or at The Rack.
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