Preppy Hats first surfaced on Chictopia's streetstyle gallery in Spring 2009 seen on Stockholm blogger sillyeuropean. She wore her beige thrifted hat with a blue second hand skoldisco blouse, black inherited skirt, and black Indiska kne high socks. Since then, Preppy Hats have grown in popularity as bloggers from Manila, Hong Kong, and London have discovered them. Popular brands of Preppy Hats are Topshop, Primark, Forever 21, vintage, and H&M.
There are currently 749 streetstyle photos of bloggers wearing Preppy Hats. Most recently, blogger Kryz of kryzuy.com rocked her black WAGW hat with a black Fashion Beauty and Beyond sweater, maroon Avon bag, and crimson Bayo skirt.