Winter Skirts first appeared on Chictopia's streetstyle gallery in Summer 2008 seen on Melbourne blogger gogosushi of leblogdesushi.com. She styled her gray Sportsgirl skirt with a black portmans scarf, black Sportsgirl jacket, and black Shoobiz boots. Since then, Winter Skirts have grown in popularity as bloggers from Los Angeles, New York, and London have discovered them. Winter Skirts are generally seen in chic, casual, and classic style. Popular brands of Winter Skirts are thrifted, vintage, Zara, Forever 21, and H&M.
There are currently 17116 streetstyle photos of bloggers wearing Winter Skirts. Most recently, blogger viewsofnow of viewsofnow.com styled her silver The Haute Pursuit bodycon miniskirt skirt with a heather gray Topshop crop top gray monochrome top.