It's been well established that we New England wasps love to sail, but even we know that you can't go everywhere in a yacht. Their great for those trips from Martha's Vineyard to Block Island, or from Sag Harbor to Nantucket, but what about when you've got to get somewhere on land, say from Greenwhich to Newport? For such a journey, only a car will do. The question is, of course, what sort of car? Only certain types will be acceptable and don't even think of mentioning a pickup truck. In the summer a convertible top is convenient, but let's remember, in New England, there are two seasons; summer and winter and New England winters tend to bring snow. Since we love to ski, of course we'll be equipped with the proper vehicle for hazardous winter road conditions - after all, we're from New England. The following cars, though, are popular among our social circles. Read on.
It's not the most expensive of transportation methods, but as far as preppy cars go, one vehicle stands above all others; the Volvo Wagon. Their not quite as sleek and stylish as some other cars that we'll get to shortly, but these beauties have a cache all their own. Yes, they run forever, as all volvos do, but their also great in the snow, which is a definite plus for those who love to ski. Other volvo models are models are popular as well, but these wagons are classic, as they have certainly endured throughout the ages. It could be argued that the standard volvo wagon falls into the same category as the green Barbour jacket as something that every New England prep school student owns. While some families have always owned more expensive cars, such as BMWs, make no mistake; if you ever went to a private school in New England, your parents had one of these. 
Although your parents doubtless had a Volvo Wagon if you went to prep school in New England, if you can from money, the BMW was the car that they bought you as a reward for getting your license. Chances are, your old man had a beamer that he loved too. It was probably used, but it was classic. There can be no doubt that the BMW is the classic car of the waspy types, particularly those from New England, and for good reason; their the best. Although their fellow German-made brands, Audi and Mercedes-Benz are popular with preppy crowd, throughout the years, BMW has always been the popular choice. When your parents are paying for your first car, there's typically plenty of choice, but it's hard to turn-down a car as great and as classy as the BMW. Beamer convertibles are popular as well, but typically more so on the west coast, with it's nice weather.
If your folks were making you pay for your own first car, though, or if the Beamer or Benz were out of your price range, the go-to choice was always the Volkswagon Golf. Given the fact that it's the only car with the word "golf" in the title, it would certainly make sense that this car would be popular with the waspy preps, I mean, what else would you show up at your parents country club in? The cabrio convertible probably makes the most sense for a lifestyle like that; just pop the top, toss your clubs in the back and you're good to go - white (as pictured) is probably the preppiest color for this type of car and it is certainly the most popular. This was personally the first type of car my father thought of for me.
The volvo, the beamer, and the golf tend to fairly small cars, which clearly don't work for everyone. If you're a bigger guy, say a prep school lax bro, you'd need a bigger ride and that's where our next vehicle comes in. If you're the type of who divides his time between the lacrosse field and his prep school's gym, then the Mercedes-Benz G-Wagon would be a popular choice. Classier than a Range Rover, this car is particularly popular among two very different types of people; prep school jocks and Russian mobsters. Long Island lax bros seem to be particularly fond of the G-Wagon, although they may not always realize that the G doesn't stand for what they think it does. If you're the type of prep who likes to grab your bros and make a drive from your school in the Connecticut countryside to your family's beach house in the Hamptons, this may just be the car for you.
Let us not forget though, that not every prep's sound home is on the ocean. Indeed their are families who prefer a quiet cottage on a nice lake in Maine, and for their children, a Jeep Wagoner makes the most sense as far as cars go. Much classier than a Subaru, this vehicle is known for it's classic wooden siding, but also comes with a very comfortable interior and great off-road capibilities, making it ideal for those tough back roads that lead to your families lakeside cottage and you wouldn't want to drive the new Beamer on. The driver of a car such as this would typically be clad in an L.L. Bean Norwegian sweater, a bottle-green Barbour jacket, and J. McClaughlin khakis with a duck or bird-dog pattern and classic Bean Boots from L.L. Bean. The Wagoner also has plenty of space in the back for the yellow lab or your friends from Hotchkiss. For an afternoon of quail hunting, there's really no better car than the wagoner.
Honorable Mentions -
The Range Rover
The Land Rover
The Volvo Estate
The Saab 900
