Here, in the richest town in the U.S., everyone owns houses bigger than most apartment complexes and drive cars that are more expensive than houses in "the rest" of America. 99% of the town is white, and all the girls wear lacoste and ralph lauren polos and oxfords (collars popped -- that's a given), j. crew classics, "real" juicy couture, and accessorize with prada. Knockoffs? What are those?! After lacrosse or field hockey practice, they all top off their polka-dot hair ribbons with eliza b. or rainbow flip flops. Don't even think about wearing just red or blue, it's all "nantucket red" and "lagoon" or "ocean spray".
Now onto the boys they date:
All wear seersucker or madras shorts/pants, and have long, stylishly unkempt hair. They all sail and play lacrosse, and are exceptional at both, when they aren't stoned or drunk. Their families attend yacht club parties every saturday night, where all the men have names like "tyler" and preppy little nicknames.
For fun in Greenwich, girls shop 'til they drop on "the Ave", where the most popular stores include "Rags" and "Wishlist", where you can pay $70 for a faded shirt that has been "professionally aged" so that the buyer can pretend to be ghetto and poor. And "ghetto" is a word used often in Greenwich. Preppy kids dressed to impress often say things like, "woah, man, your BMW is sooo mad ghetto". For the cash it takes to buy the sportscars that are cruising around Greenwich, you could buy and refurbish a ghetto.
Bottom line: Greenwich is preppy to the max, a prime example of a community so sheltered that most of the people there have an incredibly skewed perspective of wealth.
Greenwich, the home of the plastics.