As personal expression becomes more celebrated, many of us want to showcase our unique personality through our clothing. While defining a specific style can be tough - and maybe even unnecessary - styles can generally be broken down into categories: formal (suit & tie), casual (t-shirts, jeans, sneakers), or smart casual (a mix of formal and casual). But there’s another style that’s become synonymous with youthful sophistication, once the hallmark of the intellectual and wealthy elite in America - Preppy.
What is Preppy Style?
Preppy is less about a set of rigid rules and more about an attitude. It’s a style that "elevates Casual and tones down Formal." While similar to smart casual, Preppy takes it a step further by blending formality with ease, giving off a "dapper" vibe while remaining relaxed. Preppy fashion isn’t about looking stiff - it’s about looking polished yet comfortable, with each outfit carefully curated.
The Origins of Preppy Style
Dating back to the early 20th century, Preppy first emerged around 1910 – 1912 and gained popularity under the name "Ivy style" during the 1940s and 1950s. The "Ivy" comes from the Ivy League, a group of eight prestigious northeastern U.S. universities, including Harvard, Columbia, and Princeton. These universities were known for attracting the wealthy and influential, and Preppy fashion became a symbol of academic and athletic success.
The essence of Preppy is confidence, a blend of old and new. The most important thing? You have to feel comfortable. Classic, relaxed, or even rebellious. It’s all still Preppy - a style that never lets you down." - Tommy Hilfiger.
How to Dress in True Preppy Fashion?
Today, Preppy style has become a fresh direction for streetwear enthusiasts looking for a polished yet laid-back look. Key items include:
Navy blazers
Button-down shirts
Chinos (beige or camel)
Crewneck sweaters
Loafers
Knit ties
A classic Preppy style outfit.
The classic Preppy look features a navy blazer, striped Oxford button-down shirt, and beige chinos. Accessories like watches, belts, and shoes can be personalized to reflect your personality.
Start with the basics: white button-down shirts or pastel shades like light blue, pink, and yellow. Patterns like pinstripes or checks (plaid, gingham) are also common.
A signature Preppy move? Turning a sweater into an accessory by draping it over your shoulders.
The next key piece is a pair of yellow khaki chinos paired with dark brown loafers, topped off with a navy blue blazer. For a more layered look, a cable-knit sweater with a diamond pattern is spot on! And, of course, accessories are a must. The signature Preppy accessory: a repp stripe tie, complemented by a braided leather or nylon belt.
I will summarize some key items that are characteristic of the Preppy style below:
Navy blazer with brass buttons
Button-down shirts
Polo shirts
Varsity jackets (aka Letterman jackets), often worn by athletes in baseball, football, and rugby 😁
Sweaters (crew neck, V-neck, or cardigans) in cable-knit or argyle patterns
Chinos
Loafers
Repp stripe ties
Braided belts
While Preppy style has evolved over time, with slimmer fits and more casual options like sneakers and jeans, the core items remain timeless. The goal is to invest in quality pieces that will withstand trends and last for years - maybe even passed down to future generations.
More recently, we've seen a blend of Preppy with streetwear in collections like Drake's and Aime Leon Dore's Fall/Winter 2020 line. It’s the perfect mix of classic and modern.
Brands like Ralph Lauren, Brooks Brothers, Drake’s, J. Press, J. Crew, and Tommy Hilfiger have long been associated with Preppy fashion.
Comments