Wool Hats first surfaced on Chictopia's streetstyle gallery in Spring 2009 seen on Zürich blogger PascalG. He wore his black vintage wool hat with a black Ray Ban wayfarer glasses, black selfmade jersey scarf, and black filatures du lion cashmere, cotton sweater. Since then, Wool Hats have grown in popularity as bloggers from New York, Los Angeles, and Winnipeg have discovered them. Wool Hats are generally seen in casual, bohemian, and chic style. Popular brands of Wool Hats are OASAP, asos, Forever 21, vintage, and H&M.
There are currently 619 streetstyle photos of bloggers wearing Wool Hats. Most recently, blogger Myblondegal of myblondegal.com styled her ruby red Choies wool hat with a black Kate-Katy boots, ruby red younghungryfree leather dress, and ruby red OASAP coat.