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Cashin returned to New York, and to Adler and Adler, in 1949. She received the unprecedented honor of earning both the Neiman Marcus Award and the Coty Fashion Critic's Award within the same year (1950). Displeased, however, with her manufacturer's control over her creativity, she decided to challenge the setup of the fashion industry. Working with multiple manufacturers, she designed a range of clothing at different price points, thereby specializing in complete wardrobes for "my kind of a girl for a certain kind of living."

In 1953 Cashin teamed with the leather importer and craftsman Philip Sills and initiated the use of leather for high fashion. She made her name through her unconventional choices in materials as well as her inexhaustible variations on her favorite theme of adapting the flat, graphic patterns of Asian and South American clothing to contemporary global living. Through her work for Sills and Company, she is credited with introducing "layering" into the fashion lexicon. In turn, she credited the Chinese tradition of dressing for, and interpreting the weather as, a "one-shirt day" or a "seven-shirt day." Her layered garments snugly nestled within one another and were easily converted to suit different temperatures and activities by donning or removing a layer. Cashin's objective was to create a flexible wardrobe for her own globe-trotting lifestyle, wherein seasonal changes were only a plane trip away. Frustrated by the categorization of sportswear designer, she declared that travel was her "favorite sport."

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