Pencil Skirts first surfaced on Chictopia's streetstyle gallery in Spring 2008 seen on Portland blogger camiller. She wore her American Apparel pencil skirt with a American Apparel tri-blend top, Doc Marten boots, and cynthia rowley bag. Since then, Pencil Skirts have grown in popularity as bloggers from Chicago, Los Angeles, and San Diego have discovered them. Pencil Skirts are generally seen in chic, business casual, and classic style. Popular brands of Pencil Skirts are thrifted, asos, Zara, Forever 21, and H&M.
There are currently 529 streetstyle photos of bloggers wearing Pencil Skirts. Most recently, blogger lanton of qualityrivets.blogspot.com styled her light pink Missguided pencil skirt with a black Missguided grid print sweater.