I have very skinny calves and ankles ( chicken legs) which tends to present a lot of problems when fitting boots and booties. I have recently scored Report Marks booties in taupe on great sale (#1), and there are also these cherry red Aerosoles (2) ones from a big clearance in February.

I love them both and will wear them a lot with various pants. However, I was wondering if I could get away with them with skirts since they are quite loose around the ankles. I am not particularly concerned about the leg line here, only ankle fit, as I do not want to look like I am wearing rain boots. For comparison, there is a photo of tan sandal/booties that fit they way I like around the ankle, probably because they are cut lower, under ankle bone. So, are the first 2 OK for skirts, or, once fall comes, should I look for a model like #3 but without cutouts, obviously?

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