Preppy Dresses first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on Fort Lewis blogger ClothesHorse of theclothes.blogspot.com. She wore her blue Sample pinstripe dress with a blue Ralph Lauren blazer jacket, red floral, vintage scarf, and black H&M ballet, flats shoes. Since then, Preppy Dresses have grown in popularity as bloggers from San Francisco, London, and Manila have discovered them. Popular brands of Preppy Dresses are thrifted, vintage, Zara, Forever 21, and H&M.
There are currently 2101 streetstyle photos of bloggers wearing Preppy Dresses. Most recently, blogger AnnikaVictoria wore her black Sheinside dress in a streetstyle look.