Comfortable Shorts first surfaced on Chictopia's streetstyle gallery in Spring 2008 seen on Chicago blogger thefashbot. She wore her blue Forever 21 shorts with a white Urban Outfitters striped t-shirt, gray Topshop socks, and black Urban Outfitters multistrap flats shoes. Since then, Comfortable Shorts have grown in popularity as bloggers from Manila, Los Angeles, and Philippines have discovered them. Popular brands of Comfortable Shorts are Levi's, thrifted, Zara, H&M, and Forever 21.
There are currently 7100 streetstyle photos of bloggers wearing Comfortable Shorts. Most recently, blogger nanysklozet of nanysklozet.com styled her white romwe shorts with a bronze Frye shoes, light pink romwe shirt, and bronze Pietro Alessandro bag.