Behind the Preppy Look: It's All Business

What is it about garish pink and lime green that makes for the preppy look? What is it about using a salad fork that speaks to a student's education? Are docksiders and penny loafers still the mark of a man of distinction – or, let us ask, a young man of means?

And how should one pronounce the word thermos, anyway?

The answer to all the above is yes, except for pronouncing thermos. This is an oddity among the prepster world and it is hard to name a preppy accent, but thermos does stand as a one-word litmus test. So, let's try to get it down on paper, as it were.

“As it were,” by the way, is a very preppy expression.

Back to thermos: It must be said as if a thermos was something you were fond of, even though the it is said with complete disdain. First and foremost, it rhymes with squirm. Second, you have to remove the letter “R”. The word is then spoken in the manner of a slide trombone that happens to have a British accent.

What needs to be remembered, of course, is that a prep school student is someone preparing for college and that must be more than a fact: It has to be a given, an assumption, a birthright. It is assumed that you will be going to your father's alma mater and that the said learning institution is an Ivy League school. Further, it is assumed you will protect the family legacy, which means you will more than likely go into business to protect the family assets.

Hence, to be a preppy, you are, essentially, embracing a business style but one that assumes success. 

Because preppy clothing makes use of styles that are timeless, they are viewed as conservative, given a trend setting, modern, outlandish style is not what the bankers want to see. They do not embrace risk. In fact, if you want to dress preppy, pretend you are about to go visit a bank and ask for a million dollar loan to start a business. That's how you will dress – business like, staid and slightly elegant.

This doesn't mean fun clothing is out. Preppies have off days, as well. They own old sweatshirts, hand me down sweaters with holes in them and plenty of faded blue jeans. But they also have a set of pressed pants hanging in the closet and a Navy blue jacket on hand, because it tends to go with a lot of different ensembles.

You can wear knock-offs, too, but they should be conservative. Preppy's on any given weekday wear button down shirts, pleated khakis, shined shoes and conservative ties.

On time off, they wear polo shirts, rugby shirts, shorts, sneakers, loafers. But the overall look remains conservative. Think Harvard, Yale, Brown, Dartmouth.

Money is the path to the exception. What do wealthy people do on their time off? The go on safaris, so safari outfits are instantly preppy. They might go surfing, so derivatives of surfer wear are permitted. Styles that come off a tennis court of a golf course are acceptable. Those double-breasted jackets you might see on a yacht are well received in the land of the prepsters.

Preppies have a reputation for being color blind, especially those that combine lime green with a garish pink. Let the women keep that territory for themselves. One color pink or yellow button down shirts are permissible for men, as are quiet stripes and checks, such as tattersall.

But to go preppy without trying, just think about dressing for a business day. Imagine you are going to spend the day on Wall Street and that you can say any sum of money without the words catching in your throat. That will get you part way there.