Where Preppy Comes From
Preppy is named after the private preparatory schools that fed America's Ivy League colleges. From the 1950s, students there wore oxford shirts, chinos, crew-neck sweaters and loafers, a look later called Ivy style. The 1980 book The Official Preppy Handbook made it a known style, and brands such as Ralph Lauren built on it.
Preppy overlaps with old money style. The difference is colour and energy: preppy uses more stripes, brighter colours and sporty pieces, while old money style stays quieter.
The Key Pieces
For everyone: oxford button-down shirts, polo and rugby shirts, cable-knit and V-neck sweaters, Breton stripes, a navy blazer, chinos, a quilted gilet or trench coat, penny loafers, boat shoes and white canvas sneakers. For women, also: pleated or A-line skirts, shirt dresses, cardigans, headbands and ballet flats. For men, also: chino shorts in summer, knitted ties and a waxed field jacket.
Colours: navy, white, red, kelly green, pink, light blue, khaki and cream, often in stripes or gingham.
Read more: Old Money Style for Men: The Complete Outfit Guide
How to Keep It Modern
Pair one preppy piece with plain basics: a striped rugby shirt with dark jeans and white sneakers, or a cable knit with relaxed trousers. Avoid wearing a sweater tied over your shoulders with a blazer and boat shoes all at once. Choose relaxed rather than tight fits, which look more current.
Hair that suits preppy style is neat but not stiff: a side part, an Ivy League cut, a long bob or a sleek low bun.
Try a Preppy Outfit
Preppy is one of the 9 styles in Choose for me in Ollie Stylist. It builds a full outfit on a free model set to your build and height, with links to every piece. See all 9 in aesthetic types.
Read more: Aesthetic Types: Find Your Style in 9 Looks