In 1986, the company opened a chain of clothing stores named Gymboree. Gymboree stores offered coordinating children's clothing. The sizes ranged from newborn to size ten. As of January 2019, it operated 380 Gymboree stores, 154 Gymboree outlets, 147 Janie & Jack stores, 253 Crazy 8 stores, and 11 Crazy 8 outlets in the U.S. and Canada.
Gymboree store at the Scarborough Town Centre in Toronto in 2008
Crazy 8 was started in August 2007. It featured lower-priced clothing and was Gymboree's direct competitor for The Children's Place and Old Navy.
In 2010, Bain Capital acquired the company for US$1.8 billion.
In June 2017, Gymboree announced it was filing for Chapter 11 bankruptcy protection. As part of the debt management process, it said it would close 375 of its 1,300 stores. In September 2017, the company emerged from bankruptcy. In 2017, the company closed 350 of its 1,281 stores.
In November 2018, it was reported that Gymboree would file for bankruptcy for the second time in 14 months, and as a result, Gymboree announced plans to discontinue the Crazy 8 brand and close all Crazy 8 stores after the holiday season.
On January 17, 2019, Gymboree filed for Chapter 11 bankruptcy protection, closing all Gymboree, Gymboree Outlet, and Crazy 8 stores as a result. The company sold its Janie & Jack stores to Gap, Inc.