Like nearly all artists, it took Whitmore a while to settle into a mature, characteristic style. Below, I feature examples of his earlier work. These images were competently done, but do not stand out from works of other illustrators from that era. Nevertheless, his work was already appearing in major magazines, and by the mid-1950s Coby Whitmore had truly become the Coby Whitmore we know.
The man in the upper image strikes me as looking a lot like William F. Buckley, founder of National Review.
Whitmore is already adding a dab of the risqué.
I don't know the source, but it's probably from an advertisement or perhaps a story. During World War 2 women were used to ferry aircraft from place to place around the country. A few might have been test pilots who checked out newly-built aircraft. None, so far as I know, were test pilots of the classical kind who wrung out prototype airplanes. As long as I'm being picky, pilots almost always enter the cockpit from the left side of the aircraft, not the right, as pictured here.
The woman's pose echoes the one from around 1942, above.
Whitmore did a number of covers for Cosmo in the early post-war years.
The car in the background seem oddly old-fashioned -- late 1930s styling. But Whitmore was a car guy, and must have had his reasons for including that vintage.
This image and the one above it include plenty of background detail, something unusual for Whitmore. But in the late 1940s, many art directors expected it.
At last, Whitmore gets to seriously combine his love of cars and beautiful women. The styling is imaginary, though the basic shapes are early-1950s.