I’m finding wrap skirts, short or long, very appealing. I would pair any of these with a turtleneck and be good to go. In colder climates, there’s the luxury of adding a thigh high boot while more mild temps call for either bare legs or tights. All of these skirts would look great with both ankle boots and knee high boots but I would keep the heel flat for the shorter skirts. That’s generally my rule of thumb…the shorter the hemline, the flater the heel.
Clockwise from top left photo of Calvin Klein patched leather stripe skirt: Tibi blue suede, Sea patchwork suede, Balenciaga with silver grommet, Atlantique Ascoli felted cotton, Acne Studios wool plaid, See by Chloe patch pocket with trim.
Source: photo: ©Vogue