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While I love chunky sneakers ,and think that the Air Force One is the King of comfort to boot, maybe thick of something, maybe something like Chucks, but with an anatomical insole, might work. There are cool collabs with Rick Owen and Stussy, among others, so you could still save your style.Thanks for all the recommendations! I do despair at the possibility of having to wear dad shoes, which I really don't like. Does anyone know of anything with a more slim silhouette, for example Adidas Sambas, which I find very nice. Any middle ground that anyone knows about?