My original tumblr post was here. This image was first posted on tumblr by rogerwilkerson and comes to us via notpulpcovers. Poster rogerwilkerson provided this identifying text:

Big Man On Campus, art by Dick Sargent. Detail from Saturday Evening Post cover October 17, 1959.

A gallery of Dick Sargent’s (1911-1979) Saturday Evening Post covers can be found here.