Here is a couple of quick sketches to show the Caddy tail lights in the upper location and then some "Dagmars" utilized to fill the stock tail light areas. Then tie the dagmars together with a bumper....maybe something like a 30's bumper and I thought take a 53 / 54 Chevy license plate guard and flip it upside down to give a little more detail.
Just some thoughts
Just a little history for those who may not know where the term Dagmar came from
Harley Earl was fasinated with her.....ahhhh....her charms and through his design team the 50's chrome "protrusions" were named after her
Dagmar (November 29, 1921 – October 9, 2001) was a statuesque, busty blonde personality of the 1950s. She became the first major female star of television, receiving much press coverage during that decade.
Born in Logan, West Virginia as Virginia Ruth Egnor, she went to high school in Huntington, West Virginia where she was known as Ruthie
She adopted Jennie Lewis as her stage name (taken from her real life married name, Virginia Lewis).
In 1950, when Lewis was hired by Jerry Lester for NBC's first late-night show Broadway Open House (1950-1952), he renamed her Dagmar. Lester devised the name as a satirical reference to the huge success on television of the TV series Mama (1949-57), in which the younger sister, Dagmar Hansen, was portrayed by Robin Morgan.