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Usually people say to go with the Jumbo and that is what I originally bought and didn't like it once I took it home. The Jumbo was too large for me. I felt like I was carrying a large box on my shoulders. I'm actually pleasantly surprised that most people on this thread prefer the medium! So do I! I was hesitant to buy the medium at first cause I thought I would only use it at night, but I was very wrong! I love it for the daytime as well! A few days ago, I wore my medium flap with flip flops and that even worked!