I almost ordered boots like #1 but they look like Icould only wear them with really skinny jeans (that I don,t own) or leggings or tights. If you had them how would you wear them?

If I get mid calf boots I think I would be better to get ones like #2 so jeans could tuck in. Then I thought why when I have three pairs of tall boots.
Too much the same look. I have a pair of wedge ones with a tight fit leg about 5 inch shaft. Always find them a bit awkward. They seem to work only with jeans rolled to almost the top, and sometimes get bunchie.

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