I think it works 1000%
My wife has a mid size 31mm DJ with MOP diamond marker dial. It's very elegant and she wears it every day, dress up or dress down.
However, if she ever said she wanted a GMT, Sub, Daytona, YM, Explorer for dressing down, I'd be estatic. I think it's very stylish for a chick in jeans / yoga pants etc.. to be wearing a 36-40mm mens Rolex.
My only rule would be that she should have a ladies watch for those occassions where she really needs to get dressed up.
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