Photograph by Philip Sison
Style Necessary Style

Every self-respecting preppy should have one of these

Ever clean and crisp, there is never a look more enduring and referred to as refuge for the grown man.
Giancarla Espinosa Aritao | Oct 24 2018

Having taken a back seat for several years, the American preppy style has come back with a vengeance. Here are the seven basic elements of the preppy wardrobe:

Purple, blue, and white stripe repp tie from Brooks Brothers.


A staple in many a man’s closet, the repp tie was named for the weave of silk it uses. It began as a way for British schools and soldiers to display their official colors. By the 1920s, repp ties began showing up in private clubs in order to identify and denote the status of the wearer. Ivy League students discovered the repp tie and adopted them as a fashion statement. Originally, repp ties had stripes that descended from the left, but modern versions are more varied.

Blue and white check button down shirt from Brooks Brothers.


The iconic men’s clothier Brooks Brothers, which pioneered Ivy League style and popularized madras and odd jackets, is also credited with introducing the button down shirt to Americans. In the late 1800s, while watching a polo match in England, John Brooks noticed that players buttoned their collars to prevent them from flapping as their horses galloped across the field. Within the same year, he brought back the design and had it copied for street wear. The new button down shirt, with their attached collars and cuffs, revolutionized men’s shirts, with many clothing manufacturers following suit.

Red classic polo shirt from Lacoste.


French tennis player Rene Lacoste is credited with inventing the tennis shirt. It was made out of a lightweight cotton knit and featured ribbed cuffs and a collar that can be turned up to protect the neck from the sun.  The longer shirttail allowed the player to bend over and pick up a ball without inadvertently untucking his shirt. The design was later manufactured under the company Chemise Lacoste and became hugely successful. Polo players, who previously used button down shirts, noticed how comfortable the shirt was and wore it themselves. In the early ‘70s, Ralph Lauren incorporated the design in his Polo line, sealing its popularity.

Navy blazer with embroidered pocket from Ralph Lauren.


The sports jacket evolved from the hunting attire of the Duke of Norfolk. It was originally belted, tweedy, or checked. As a hunting jacket, it featured box pleats in front and at the back to ensure that movement was not impeded. Eventually, the jacket evolved and was used in other sports such as golf. Boys from the Ivy League took the jacket out of the greens (or the wilds) and used it for laidback functions because it was more casual.

Khaki chinos with animal embroidery from Ralph Lauren.


Starting in the mid-1800s, chinos or khaki trousers were worn by the military in the United States and England. It featured no pleats, a zipper and button closure, and a slim leg. In the 1920s, khakis began popping up in campuses where denim was considered unacceptable. During the early years, khaki was actually a color before the word was used interchangeably to refer to the trousers that sported the dusty shade. In the hands of preppies, however, chinos began to sport unusual hues and prints while retaining the original fit—neither too tight nor too loose, and dropping right at the ankle or just above it.

Black penny loafers from Bass.


Loafers follow the shape of Native American moccasins. Ironically, American students touring Europe discovered them in Norway and took a shine to the low-heeled footwear that simply slipped on without buttons or closures. The penny loafer was introduced in 1936 by G.H. Bass, who gave it the name Weejun, a contraction of the word “Norwegian.” Its new feature was a split-design strap running across the top of the shoe. Students used this opening to stash money, thereby associating the penny with the shoe.

Brown brogues from Allen Edmonds.


The elite were not immune from taking something from the working class and making it their own. Brogues started out as shoes for Irish and Scottish workers out in the damp fields. The name comes from the perforations dotting the shoe in a signature pattern, which is called brogueing. These holes allowed water to drain out, making them more comfortable. Later models also had fringed tongues to increase waterproofing. Golfers discovered these heelless shoes and wore them outside the links. By the late 1920s, brogues were a staple for the disciples of prep.


Photographs by Philip Sison

This story first appeared in Vault Magazine Vol. 5 2012.