Comfy, breezy, and easy — maxi skirts are the best skirts, especially for summer. While i used to be all about the boho look of the long, flowy skirt back in my hippie. How to wear long skirts: Yes, maxi skirts in winter are definitely a thing. If you’re unsure what to wear with a maxi skirt at this time of year, a pastel pink skirt. A cardigan, like a sweater, is a garment that will keep you warm. When spring follows, a lighter cardigan can be worn through the summer. With the maxi skirt, you could. A black maxi skirt can be worn with white (or milky, beige, pale pink), jumper or cardigan. The alternative in the cold season is a black leather jacket over a beige or something.