Charming Charlie Hats first appeared on Chictopia's streetstyle gallery in Fall 2010 seen on Colts Neck blogger MaraMasonEmm. She styled her black Charming Charlie hat with a brown Goodwill sweater. Since then, Charming Charlie Hats have grown in popularity as bloggers from Snellville, Chicago, and Colts Neck have discovered them. Charming Charlie Hats are generally seen in vintage, bohemian, and chic style. Popular types of Charming Charlie Hats are black hat, paper yarn, floppy hat, cloche, and bowler. Blogger's favorite colors are black, nude, neutral, and tan.
There are currently 41 streetstyle photos of bloggers wearing Charming Charlie Hats. Most recently, blogger theamylooblog of theamylooblog.blogspot.com wore her black Charming Charlie bowler hat with a gold Candie's patent leather purse, red heart sunglasses, and black t-strap heels.