Trendy Shorts first appeared on Chictopia's streetstyle gallery in Fall 2008 seen on Adelaide blogger leflassh. She styled her Terranova light denim shorts with a white Wrangler t-shirt, white bardot blazer, and black SUPRÉ tights tights. Since then, Trendy Shorts have grown in popularity as bloggers from Los Angeles, Manila, and New York have discovered them. Popular brands of Trendy Shorts are Levi's, Topshop, Forever 21, H&M, and Zara.
There are currently 4020 streetstyle photos of bloggers wearing Trendy Shorts. Most recently, blogger corazondemaniqui of corazonmaniqui.com styled her gray Promod shorts with a black trendy too boots and gray Promod sweater.