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 Hong Kong, Manila, and Winnipeg have discovered them. Popular brands of Preppy Hats are Topshop, Primark, Forever 21, vintage, and H&M.
There are currently 803 streetstyle photos of bloggers wearing Preppy Hats. Most recently, blogger mayo_wo of mellowmayo.com styled her navy Bernstock Speirs hat with a white the layers shirt, brick red Saint Laurent bag, and bubble gum the layers socks.