Excellence of taste in the fine arts and humanities, also known as high culture
Although it is hard to define what “preppy” music is, there are a few bands that come to mind when one defines a “prep”.
Think classic “1920s”: Jazz & Ragtime. The roaring twenties. Combined with the original preppy, the 1950s: Blues, Pop (Frank, Tony, etc), and Country.
The Preppy Life wrote a blog post on the “Top Preppy Albums of the Unnamed Decade” which you can read here.
College Prepster (taken from Unabashedly Prep) has recently started posting Playlists which you can see here. She also wrote an article on her “soundtrack”, and an article on what Pandora stations she listens to.
Unabashedly Prep has dedicated an entire section of his website to “Music and Books”. You can view this section here. This covers both classic books, such as the Great Gatsby, and preppy guides such as the Bill of Rites.
These magazines might not necessarily be ‘entirely’ preppy, however they are fashion magazines that focus on a more classy and refined style. For more specifically “preppy style” magazines, I would suggest subscribing to J.Crew/Vineyard Vines/Brooks Brothers catalogues.
“Preppy” movies are another hard topic to define. It is worth noting, however, that the “preppy” fashion came into existence around the 1950s (originally: Ivy League style). The 1950s were dominated by Elizabeth Taylor, Marilyn Monroe, Jane Russell, Montgomery Clift, Marlon Brando, James Dean, Harry Belafonte, Humphrey Bogart, and so on. Thus, any movie involving the above mentioned could be considered preppy.
If you want to check out a few more lists of “preppy” movies I have found a few links which are listed below.
The Preppy Life wrote an article on the “Top 10 Preppy Movies”
Ivy-Style.com has tagged the blog posts which include mention of preppy movies.