These wonderful photos sent me digging into Kay Windsor's background, and an interesting one it is. The company Kay Windsor Frocks, Inc began in 1939 by now 97-year-old Carl Shapiro and his father. It was a Boston company specializing in "a nationally-advertised line of medium-priced dresses and suit-dresses for women and girls of all ages and sizes".
Shapiro's father was a Polish immigrant and pattern maker, and the two began a challenging marketing campaign - to elevate the dowdy cotton house dress to a charming, chic status. Their dresses were accessible in price (from $8.95 to 14.95) as well as stylish and comfortable. The Shapiros were shrewd businessmen. By 1959 the business had 22 factories throughout New England, all manufacturing primarily cotton day dresses, and Kay Windsor was a national success story.
The slogan most often seen in a Kay Windsor dress is "The Look You Love", though earlier collections focused on secretary themes. "Private Secretary" and "Secretary of the Month" are labels occasionally found from the 1940s and 50s. Because the dresses were moderately-priced and every stitch cost, the labels themselves were sewn only along the top and are often quite frayed to the sides from washings.
Like so many ready-to-wear companies, Kay Windsor designs followed fashion reliably but its chic image faded as the years passed. By the time Kay Windsor's last designs were made in 1982, those attracted to the label had aged along with it. Ironically, the final few years of the label produced mostly synthetic and dowdy designs, quite different than these glossy cotton-clad vixens from Kay Windsor's heyday.
Sources -
Lizzie Bramlett's post:
http://vintagefashionguild.org/label-resource/windsor-kay/
SEC Digest:
http://www.sec.gov/news/digest/1961/dig092961.pdf
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