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While it can seem next to impossible to find a heel that’s both chic AND comfy, they’re definitely out there—even if it takes endless internet searching to stumble across ’em. Just as comfy as your typical flip flop, but chicer, of course. Product Rating: 4.3333 of 5 stars Rating, 4.3 out of 5 stars. And whether you’re already a huge fan of heels or typically stay away, the summer 2020 high heels trends are here to help anyone understand why they’re such an integral part of fashion … your own Pins on Pinterest $37.99 $ 37. Yes. 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Lucky for you, we’ve already done the work and compiled a list of the 25 most comfortable high heels in various silhouettes, textures, and heights. The tried and tested heels for walking pain- and blister-free. Promise.