In the 1980s, Payless was widely known in the U.S. for its Pro Wings line of discount sneakers, which often had Velcro straps instead of laces.

Pay-Less National was founded in 1956 in Topeka, Kansas, by two cousins, Louis and Shaol Pozez, to open self-service stores selling budget footwear.

The St. Louis operation of "'Hill Brothers Self Service'" stores were known for their bare bones minimalism and the slogan "two for five – man alive!

[11] On June 27, 2006, Payless announced that it was launching a new logo created to represent a more stylish, upscale and contemporary company.

[citation needed] In 2018, the company advertised under a stunt premium banner, Palessi Shoes, to demonstrate that its products could pass for high-end designer brands.

[13] In April 2017, the company, struggling with the migration of retail shopping to e-commerce, filed for Chapter 11 bankruptcy[14] and closed 673 stores nationwide.

[15] Prior to the bankruptcy, heavily loaded with debt due to a private equity buy out, the company's credit rating was downgraded by Moody's.

It also announced plans to open between 300 and 500 free-standing stores in North America over the next five years[24] and relocated its company headquarters from Topeka, Kansas to Edgewater, Florida.

[25] Collective Brands, Inc. was an American holding company that owned Payless ShoeSource, Robeez, and Airwalk.

[29] Stride Rite Corporation purchased the Sperry Top-Sider and Keds brand names from Uniroyal in 1979.

[32][33][34] On July 14, 2014, Authentic Brands Group acquired some assets from Payless's division Collective Licensing International, LLC.