Checkered Skirts first appeared on Chictopia's streetstyle gallery in Fall 2008 seen on Lancaster blogger ClothesHorse of theclothes.blogspot.com. She styled her blue Forever 21 checkered skirt with a gray Zara shirt, black H&M cardigan sweater, and red Urban Outfitters peeptoe, flats shoes. Since then, Checkered Skirts have grown in popularity as bloggers from Copenhagen, London, and Manila have discovered them. Checkered Skirts are generally seen in chic, preppy, and casual style. Popular brands of Checkered Skirts are asos, Topshop, Forever 21, thrifted, and vintage.
There are currently 133 streetstyle photos of bloggers wearing Checkered Skirts. Most recently, blogger viewsofnow of viewsofnow.com rocked her white Missguided checkered skirt with a black Missguided black and white top and white Nine West heels heels.