Rockwell Files: Trying on the Future

As he did in many of his covers, Rockwell contrasts between the old and the new in this painting for the March 19, 1949, issue.

The old is represented by a young woman wearing faded blue jeans, work shirt, and bobby sox and loafers, which would identify her as a tomboy. The term was once freely applied to girls who liked durable, comfortable clothing and outdoor or athletic activities. (Such traits are so common today, the term is almost meaningless.)

The new is seen in the gown she holds up to herself as she regards the complete effect in a mirror. She probably owns only a few outfits, judging from the hanger space in her closet, and this dress will certainly seem out of place when she hangs it up.

Another artist might have made this a moment of dreamy sentimentality for the girl. But Rockwell is better than that. He gives her the same expression he uses five years later on a much younger girl who studies her face in the mirror. The look is neither delighted or disapproving, but thoughtful, as if imagining how it will look on her and also what it represents.

This article is featured in the July/August 2025 issue of The Saturday Evening Post. Subscribe to the magazine for more art, inspiring stories, fiction, humor, and features from our archives.