Preppy Dresses first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on Lancaster 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 Los Angeles, San Francisco, and London have discovered them. Popular brands of Preppy Dresses are vintage, thrifted, Zara, Forever 21, and H&M.
There are currently 2305 streetstyle photos of bloggers wearing Preppy Dresses. Most recently, blogger nanysklozet of nanysklozet.com styled her light blue romwe dress with a red Spiegel shoes, cream Forever 21 sweater, and black Marc by Marc Jacobs bag.