As I worked on the written part of the presentation, I really understood more about why Esquire changed dramatically between 1945-1955. Not only did technology give them more freedom, but also the introduction on a new art director that saw things very differently: Henry Wolf. He was an Austrian emigre and brought European modernism to the magazine.
He approached covers with a concept, not just saying, "Well, let's just do a cute painting." (Which is what the previous standard was.) Wolf brought wit and cleverness to his design and enforced more typographic style.
This is a really great site to look at all the covers of Esquire. The ones between 1952 and 1958 are Wolf's work.
He moved on to Harper's in 1958, so the work there is similar to these Esquire covers. It just fascinates me how much one person can revolutionize a magazine. He worked as a lowly junior promotions designer, and one day promoted to art director by the editor. (So there's hope for all of us.)
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