The 1940s ushered a move to New York and work for the Charles E. Cooper Studio where the artist excelled drawing lovely women for various publications. Covers and inside pages of America's most popular magazines including, The Ladie's Home Journal, Good Housekeeping, Cosmopolitan, and McCall's soon followed. Sexy, beautifully dressed, classy women were his speciality that made Whitmore a true "star", though his male counterparts were always as dashing and sophisticated. If art imitates life, Whitmore's great success provided him the lifestyle he often created on canvas. Traveling the world, racing cars, was now all within his grasp, even as he moved his family to Hilton Head Island in the late 1960s to finally specialize in painting portraits.