An interesting Norman Rockwell illustration that seems to present us with a man who seems a bit older than the typical (Ivy League) undergraduate. Maybe this guy is taking advantage of the Post-WWII G.I. Bill to broaden his mind?
While the Average Guy's Guide to Classic Style does not have the American preppy aesthetic as its stated focus, there is admittedly some overlap now that I think about it. That must be the subconscious result of where and how I grew up (the Greater Philadelphia area with a healthy dose of genteel North Carolina thrown in). We certainly never thought of ourselves as preppy in any overt way though. But the look, lifestyle, and more favorable modes of thought were definitely there come to think of it. Even if I did sport BIG 80s rocker hair for several years as a teenager. No digitized photos to share here, sorry!
It should come as no surprise, returning to the point at hand, that yours truly checks in occasionally at several of the better such "preppy" blogs out there. Muffy Aldrich of The Daily Prep expressed some interesting and cogent thoughts about clothing and style in her July 15th, 2013 post, entitled Do We Dare Criticize Clothes?. Extremely well stated and thought provoking. You'd do well to check it out even if the preppy look isn't your particular thing.