Comfortable Hats first appeared on Chictopia's streetstyle gallery in Summer 2008 seen on Houston blogger MichelleYue of missnonhuman.blogspot.com. She styled her beige Forever 21 hat with a gray American Apparel cardigan jacket, blue Marc by Marc Jacobs jeans, and black tory burch flats shoes. Since then, Comfortable Hats have grown in popularity as bloggers from Los Angeles, Manila, and New York have discovered them. Popular brands of Comfortable Hats are Zara, Urban Outfitters, vintage, Forever 21, and H&M.
There are currently 3544 streetstyle photos of bloggers wearing Comfortable Hats. Most recently, blogger nightcap rocked her free people felt hat with a thrifted vintage combat boots boots, Topshop denim jeans, and modcloth plaid shirt top.