I wear shoes/boots 10.5 which requires a large size according to the Darn Tough size chart. The problem with the big ones is that they were a bit too long and had a too wide toe box in the forefoot and I have a wide forefoot! They went on slightly, but as they stretched a bit over the course of an hour, they began to stick together at the toes, especially on the outside near the smaller toes. I've never had this problem with socks. Most large socks are a size 9.5-12 and have good stretch/pull to fit, but they don't stretch/pull much so I had to downsize them to medium. They fit a bit tighter when you put them on, but not enough to be a problem. I don't notice that they get tighter as soon as I put the shoes on, probably because they stretch after a few minutes, and I don't feel anything uncomfortable during the day. UPDATE: I noticed that the stitching seemed to have stretched near the big toe, suggesting the mediums are actually a bit short for my foot. After my experience had shown that the Large was too big, I decided to take another chance and try the Large in the Light Cushion. And now the Plus Size Light Cushion really fits exactly as it should. Firmer and more precise in length than the large pillow I've tried before. I've come to the conclusion that the problem with the cushion model is that it has too much padding, causing it to crease in the toe area, which makes me feel like the toe box is too big. So for me it's the Light Cushion model.
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