With its beginnings on preparatory private school and Ivy League campuses of northeast America in the twenties, the preppy look coalesced into a recognisable style between the twenties and the fifties. Decidedly different from the more stately style of English colleges, the “New England” alternative offered softer lines and more casual combinations that are versatile in summer or winter, field or classroom, sailboat or saddle.

Propelled by the ascendancy of post-war America and the prestige of these colleges in sport and education, the “good schoolboy” image truly burgeoned into a popular style in the 1950s. It experienced a revival in the 1970s as designers made the look simultaneously more established on runways, and more accessible to the world by adopting its cues to create the simpler ensembles we see today.


The preppy guy most likely picked up his sense of style from campus, but with the diversity in colleges nowadays its popularity has waned. Nonetheless, the preppy look still has its charm for guys who like to convey a sophisticated but relaxed sensibility in their dress. Related to the preppy look is the “geek” or “nerd”, popularized in the last decade by such hit American TV series as Big Bang Theory as well as wildly successful college romance dramas from South Korea such as Dream High. Backed by black thick-rimmed glasses and star power from Joseph Gordon-Levitt, Zachary Quinto, Lee Jong Suk and Kim Soo Hyun, it’s a style that says brainy is sexy.


The preppy look reflects the traditional upper-class activities and sports of the New England region, including tennis, lacrosse, fencing, sailing, polo, crew rowing, and rugby. A typical ensemble consists of a lightly constructed cotton blazer in navy, paired with brightly coloured pants and penny loafers or boat shoes – sockless, of course.

Shirts with distinct vertical striping or gingham patterns are favoured, usually paired with chino shorts and a leather belt. As with collegiate traditions, it’s not hard to find sweaters and blazers that carry prominent seals and emblems, and ties or bowties with twin-color striping. Wearing a sweater over shirt and tie is also popular.


With its prescribed modes, the style can be put together without too much of a headache, and is perfect for men who wish to try a different look but don’t have the time for trial and error. While the preppy look does have its signature patterns, you may be surprised to find enough in your existing wardrobe to create an ensemble.


The good thing about the preppy look is that it is versatile for any climate – and items used in the summer can be layered under when winter comes. If you’re new to it, go for a light-colored striped oxford shirt, some dark blue chinos and a pair of chocolate loafers. It’ll be a good starting point to build your wardrobe from! If you’re into the nerd look, make sure it’s more than just the glasses: pair them with well-made collared shirts and a statement bowtie (stripes, dots, whatever!) to add some character.


  • J. Press
  • Brooks Brothers
  • Ralph Lauren
  • Tommy Hilfiger
  • Lacoste
  • Paul Smith
  • Sperry’s
  • Bass Shoes
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