Payless Shorts first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on New York blogger Bonnie of flashesofstyle.blogspot.com. She wore her Payless shorts with a Forever 21 dress, vintage bag, and aa pants. Since then, Payless Shorts have grown in popularity as bloggers from New York, Bronx, and Boston have discovered them. Payless Shorts are generally seen in business casual, urban, and bohemian style. A popular type of Payless Shorts are mary jane heels. Blogger's favorite colors are black and brown.
There are currently 6 streetstyle photos of bloggers wearing Payless Shorts. Most recently, blogger idee_geniale of ideegeniale.blogspot.com wore her brown Payless shorts with a white Levis cropped jeans, beige kensie top, and blue Forever 21 denim vest.