With its thoughtful nonchalance, the preppy style has captivated both men and women since its emergence in the mid-20th century. Preppy’s exclusive aura, as well as its often quite relaxed way of dressing, has meant that it has spread far beyond the circles of affluent youth on the American East Coast, where it all began.

Preppy is a term that is widely coined and which can be said to have undergone a certain amount of inflation throughout the years. Therefore, we look at a few good examples and some key garments you should invest in to piece the style together.

Three icons that paved the way for the preppy style

To get a grip on the preppy style, we begin by looking at three style icons that are known for their individual styles, and were pivotal in the development of the style.

John F. Kennedy

As a true preppy, having studied at the East Coast’s Harvard, John F. Kennedy has pathed the way for the preppy style. In a relaxed and sophisticated outfit, he embodies the casual aspects of preppy, here on the right aboard his sailing yacht Manitou.

Woody Allen

With a penchant for tweed, corduroy and cardigans, Woody Allen’s preppy style can be simplified in a delightfully geeky way without taking the outfit to any colourful extremes. You see examples of his appreciation of button down shirts, striped ties as well as a pair of khaki trousers.

Paul Newman

Often seen wearing tucked-in Oxford shirts, light twill trousers and shoes such as sneakers or penny loafers, Paul Newman’s style was inspired by the preppy style. Especially distinctive are his elements of preppy during the late 1950s, where he shows an adult approach to a preppy style.

Preppy garments you cannot live without

All styles have key garments, and the preppy style is no exception. Here is a list of some of the most important garments to own, should you wish to piece a preppy outfit together.

Preppy shirts

The Oxford shirt is a classic garment that was designed by Brooks Brothers in 1896 and has become a firm favorite in the preppy style.

Preppy pullovers/sweaters

The cable knitted pullover/sweater is a classic in the majority of wardrobes, even preppy’s. Pair with a shirt and a tie if it is a V-neck.

The polo shirt is another garment for those who want to dress like a true East Coast preppy. Wear tucked in a pair of chinos or formal trousers.

Blending in sporty influences in your dressy outfits is something that belongs to a more relaxed preppy style. Forget everything relating to clothes technology and synthetic materials. Instead, invest in classic sports garments in durable cotton such as a Rugby shirt or sweatshirt.

Preppy trousers

Chinos were brought to campus and became part of the preppy style after World War II when returning soldiers from the Pacific front brought the khaki trousers into civilian life. An obvious choice for those who want to dress preppy.

Colourful shorts perhaps fit the stereotype of the preppy style. These trousers, sometimes even with different types of embroidery, are a colourful statement in a style that requires a personal touch.

Preppy shoes

The penny loafer is the stand-alone choice of formal shoes when it comes to piecing together a dressy preppy style. The shoes were a favourite amongst American youths throughout the 50s and 60s, and fit perfectly with a pair of chinos and a blazer.

Boat shoes belong to the relaxed leisure clothing aspects of preppy. They are a stylish accompaniment to wear together with a madras shirt and a cable knit pullover.

Preppy’s formal garments

A navy blue blazer with brass buttons links seamlessly with the Ivy League Universities and the preppy style. The garment has clear references to the style’s origins from the academic world.

The stripy tie is as much a part of the preppy style as the Oxford shirt, and should be one of the first ties you invest in, should be interested in the formal preppy style.

In addition to the above garments, there is a plethora of other garments that through the years have become connected to preppy. You can explore more of them through the link below.