A few months back (a lifetime in blog-years [nice -ed.]) AContinuousLean posted Could This Be The Preppiest Movie Ever, citing the modern classic Trading Places. Cracking. I have a stealth pick though for the everyman preppy; Splash. Hear me out...
Morning suit on the beach in Cape Cod (sidenote;
Sidenote: this was the first vhs movie we owned (second was Trading Places I think) back when a 'remote' for your vcr was a 6foot cable. I think I can repeat both movies verbatum...