Preppy Skirts first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on Los Angeles blogger taghrid of taghrid.cc. She wore her white f21 skirt with a beige Target isaac mizrahi sweater, brown vintage belt, and brown Nine West shoes. Since then, Preppy Skirts have grown in popularity as bloggers from London, Hong Kong, and Los Angeles have discovered them. Popular brands of Preppy Skirts are thrifted, vintage, Zara, H&M, and Forever 21.
There are currently 3293 streetstyle photos of bloggers wearing Preppy Skirts. Most recently, blogger mayo_wo of mellowmayo.com styled her periwinkle Chicwish skirt with a mustard Miu Miu bag and burnt orange awwdore socks.