As individuality continues to dominate the fashion world, everyone strives to reflect their personality through what they wear. While pinpointing a specific style can be tricky - and maybe even unnecessary - outfits are often categorized into formal (suits and ties), casual (T-shirts, jeans, sneakers), or smart casual (a mix of both). Yet, there's another style that once defined the intellectual and affluent class in America - one that stands apart from oversized suits and flashy luxury watches. Enter the youthful, sophisticated Preppy style.
What is Preppy?
Preppy isn't a strict set of rules; it's more of an attitude. The concept is simple: elevate casual and tone down formal.
Compared to smart casual, Preppy takes things up a notch, leaning closer to formal wear but with an effortless, laid-back vibe. It exudes comfort and ease, but there’s a meticulous attention to detail behind each outfit choice.
The Origins of Preppy Style
To understand where it all started, we have to travel back to the early 20th century, around 1910-1912. Preppy first gained traction under the name "Ivy style" in the 1940s and 1950s. The term Ivy refers to the Ivy League, a collection of elite universities in the Northeastern U.S., such as Harvard, Yale, and Princeton. These institutions were home to young, upper-class students who excelled not just academically but also in sports.
Preppy style was born out of this unique combination of intellectual prowess and athletic success. Traditional sports like tennis, golf, rowing, and polo thrived on these campuses, leading to a wardrobe that catered to both academic and sporting life.
"The essence of Preppy is confidence, a blend of old and new. The most important thing? You must feel comfortable. Classic, relaxed, or even rebellious - it’s still Preppy. This style never disappoints."
Tommy Hilfiger
How to Master the Preppy Look
Preppy style offers a refined yet relaxed look for those who want to elevate their casual wear without going full formal.
The Preppy wardrobe essentials include: navy blue blazers, button-down shirts, chinos (in beige or camel), pullover sweaters, loafers, and knit ties. A quintessential Preppy outfit might consist of a navy blazer, a striped Oxford button-down, and beige chinos. The accessories and shoes allow for personal expression, adding a touch of individuality.
The Classic Preppy Outfit.
Start with the basics - white or pastel-colored button-down shirts (think light blue, pink, or yellow), then experiment with patterns like pinstripes or plaid.
Preppy enthusiasts are also known for draping sweaters over their shoulders as a style statement.
Next up, grab a pair of yellow khaki chinos and dark brown loafers, then throw on a navy blue blazer. For layering, opt for cable-knit or argyle sweaters. Accessories are key to nailing the look. The signature Preppy accessory is the repp stripe tie, often paired with woven leather or canvas belts.
Essential Preppy Items:
Navy blue blazer with brass buttons.
Button-down shirts.
Polo shirts.
Varsity jackets (Letterman jackets), which originated from baseball, football, and rugby uniforms
Sweaters (crew neck, V-neck, cardigans) with cable-knit or argyle patterns
Chinos.
Loafers.
Repp stripe ties.
Woven belts.
Preppy mixing has stayed relatively consistent over the years, though slim-fit clothing has gained popularity. Some modern touches include sneakers, boat shoes (though not my personal favorite 😅), jeans, and more vibrant patterns, though the color palette still tends toward muted tones. My advice? Invest in timeless pieces that transcend trends - you might even hand them down to future generations.
Preppy Style Meets Streetwear: Drake's and Aime Leon Dore Fall/Winter 2020 Collection
If you’re looking to stock your wardrobe with Preppy essentials, brands like Ralph Lauren, Brooks Brothers, Drake's, J. Press, J. Crew, and Tommy Hilfiger are great starting points.
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