What particular songs or genres of music would be described as 'Preppy'?

Someone posted a list online some years ago, listing “The Top 10 most Preppy Songs.”

Several repliers, myself foremost, strongly disagreed, saying that six of those ten songs were urban, hip-hop, whatever. Two were kind of Hipster / Alternative – the final two were artsy hipster types like one might hear / download at Starbucks.

All of this music was good as far as the aptitude and artistic ability goes into those specific genres. Maybe they were heard / listed at Abercrombie & Fitch which at one time showcased neo-preppy clothing.

I would like to briefly define “Prep” and “Preppy” as what once was Ivy League; an old-money lifestyle, in the States it might exist among the coasts. Authentic “Preppy style” is something one must be born into. It is badly emulated by many fakers and posers but is also emulated by those who wish to adopt it for its traditional, coastal, high-end qualities.

It was best exemplified to those of us like myself who are outsiders by The Official Preppy Handbook by Lisa Birnbach – described as a facetious guide to emulating the look, speech patterns, thinking, and lifestyle of those who attend prep schools and are a part of high society.

At one time, it was considered WASPy (White, Anglo-Saxon, Protestant) – but as coastal people with money are very liberal in their ties it has become increasingly multicultural, as even Birnback now affirms.

The only music I was able to suggest was ‘Preppy’ might be some of the Beach Boys songs regarding sailing. Or perhaps Peggy Lee’s “Is that all there is.”

So, what are some songs that would define Preppy, High Society, Old Ivy?