Always underdress. The goal is not to look as if you made an effort for the particular event. If you can dress for a different party (i.e., wear black tie to a cocktail party, or tennis clothes for lunch), so much the better. You give the impression of being much in demand.

Even if you're starting from scratch and buying a new wardrobe, preppy clothes are very fairly priced compared to high fashion. They're very easy to absorb into your wardrobe. You probably already have stuff you can wear and there's a safety factor. You're dressed for success, in a way, if you look like you grew up with success.

A tip: if you're invited to your friend's country club to go the lost and found bin and pretend that you left something there. Next thing you know, you have a fabulous sweater.

Cynicism is more than a pose it's also a handy time saver. By deflating your companion's enthusiasm, you can cut conversations in half.

Dartmouth Winter Carnival opens, proving once again that bitter cold is no obstacle to going completely out of control.

Wool, cotton, and the odd bits of silk and cashmere are the only acceptable materials for Prep clothes. They look better. They require professional maintenance. They are more expensive.

The University of Miami is not a campus with visible school spirit, just visible tan lines.

Looking, acting, and ultimately being Prep is not restricted to an elite minority lucky enough to attend prestigious private schools, just because an ancestor or two happened to arrive here on the Mayflower. You don't even have to be a registered Republican.

It is the inalienable right of every man, woman, and child to wear khaki.

In a true democracy everyone can be upper class and live in Connecticut.