Preppy Shirts first surfaced on Chictopia's streetstyle gallery in Spring 2008 seen on Loma Linda blogger fashionispoison. She wore her gray American Red Cross from target shirt with a black Cavalli for H&M blazer, brown Zara shoes, and yellow Vintage, Forever21, Ron Herman, H&M accessories. Since then, Preppy Shirts have grown in popularity as bloggers from Los Angeles, London, and San Francisco have discovered them. Popular brands of Preppy Shirts are thrifted, Ralph Lauren, Forever 21, Zara, and H&M.
There are currently 2765 streetstyle photos of bloggers wearing Preppy Shirts. Most recently, blogger districtofchic of districtofchic.com wore her neutral Equipment button down shirt with a navy H&M skinny jeans jeans, hot pink neiman marcus cashmere sweater, and navy Zara double-breasted blazer.