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What body type can wear a midcalf boot either with tucked in jeans or skirts (if that ever works. I admit, I have done both but don't know if it worked.
Are there guidelines?
I've really no idea gg, so I can't help you out here, but I just found this thread in which Angie says that there are too much variables at play to establish general rules:
I don't think I ever read that. I do have thin calves so I think that I will play around with this. I have some mid calf boots that I have just been wearing with bootcuts.