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, San Francisco, and London have discovered them. Popular brands of Preppy Shirts are Tommy Hilfiger, Ralph Lauren, Forever 21, Zara, and H&M.
There are currently 2545 streetstyle photos of bloggers wearing Preppy Shirts. Most recently, blogger FashionisaPlayground of fashionisaplayground.com styled her Claudie Pierlot shirt with a Sheinside.com coat, American Apparel jumper, and Zara pants.