Anthropologie Weave the Ring Skirt

Does anyone else have this skirt?
I have worn it in the summer, but I'm wondering if you guys have any suggestions for wearing in colder weather. It's so cute! I'm thinking maybe some brown boots. But then would that look too Laura Ingalls Wilder-ish? Any suggestions would be great! I'm gonna try some stuff on with it and experiment. We shall see how it goes. . .
I love how the model looks in this picture though. However, I don't think I could pull it off. Besides the fact that I don't have a button up shirt like that, or shoes like that!

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