Cynthia Rowley, the 2025 CFDA Eleanor Lambert Founders Award Honoree, has successfully packaged fashions joie de vivre for four decades and counting.

The Chicago natives fashion fame began serendipitously in the early 1980s when her own self-designed outfit caught the eye of a Marshall Field’s department store buyer during a subway ride. The chance encounter sparked her first collection. Rowley would later tell WWD, “I didn’t even know what a [fashion] line was, back then.”

Her brand’s evolution was captured over four decades in WWD’s coverage, including in its reporting of the Chicago fashion market. One of Rowley’s first showings was with the Chicago 21, a collective of 21 young designers who banded together in 1982 to show the industry they were a national fashion force. She moved to New York a year later. Her affordable yet contemporary fashion embraced a modern playfulness, making her a Seventh Avenue favorite.

By the 2000s, the brand began leaning into lifestyle licensing, tapping into every fashion category—including baby gear—and helped revolutionize the pop-up shop experience, delighting old and new fans around the globe. Rowley’s signature “fun” element remains uniquely hers—few designers could roller skate or ride a bicycle down a runway to applause.

In celebration of Rowley’s CFDA honor, WWD and the Fairchild Archive take a retrospective look at her signature fashion collections and iconic runway moments.