(The "Winnie" — to an individual selected as the leading designer of American women's fashions)

1950 —Charles James

Bonnie Cashin

1951 —Jane Derby

1952 — Ben Zuckerman

Ben Sommers

1953 — Thomas F. Brigance

1954 — James Galanos

1955 — Anne Klein

Jeanne Campbell

Herbert Kasper

1956 — Luis Estevez

Sally Victor

1957 — Leslie Morris

Sydney Wragge

1958 — Arnold Scaasi

1959 — No Award