Trendy Hats first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on Chattanooga blogger Snowshoe. She wore her black Forever 21 bowler hat with a black American Apparel t-shirt dress, gray thrifted drapey tank top, and black Forever 21 booties shoes. Since then, Trendy Hats have grown in popularity as bloggers from Los Angeles, New York, and Manila have discovered them. Popular brands of Trendy Hats are Urban Outfitters, vintage, Zara, Forever 21, and H&M.
There are currently 1997 streetstyle photos of bloggers wearing Trendy Hats. Most recently, blogger QQHAN of youtube.com/2qhan styled her Chicwish floral floppy hat hat with a Chicwish silver boots boots, Chicwish knitted dress dress, and Q2HAN cardigan cardigan.