Preppy – When people talk about preppy style, they nod to the young New Englanders from old money who came up with the look a century ago. “Prep” was short for prep school and aspirations toward the Ivy League. As time passed, the preppy style was adopted and adapted by all kinds of people, from hip-hop artists to Midwestern teenagers.
Ralph Lauren, Tommy Hilfiger, Brooks Brothers and J. Crew popularized sweaters, button-down shirts and boat shoes. Today, Thom Brown and Noah bring fresh takes on the look to a new generation. What started as a mark of exclusivity has become subversive and urban. Contemporary preppy style is inclusive and all about bold self-expression. Here are nine preppy must-haves for your wardrobe that range from cute shoes to stylish patterns.
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Argyle is a confident pattern. You can play it straight in gray and navy or give it an edge with bright, high-contrast color. This Scottish motif has been endlessly adapted by designers all over the world, but preps keep it classic with alternating columns of equally sized diamonds worn with jeans, trousers or a pleated skirt. To bring this signature element of preppy style into your look, choose a sweater or sweater vest, or take it to the next level with a midi dress.
From penny loafers to driving shoes in leather, suede or vegan options, fashionable shoes like loafers have become iconic elements of thoughtful everyday style. These comfortable shoes speak to tradition, heritage and craftsmanship, but recent versions have made a more assertive statement with chunky soles and oversized hardware.
Loafers look great with khakis, and they can also be styled with dresses. You can pick a trendy or traditional pair, but a true aficionado of preppy style will pay attention to quality, shape and detail to perfectly ground their ensemble.
Think of a blazer as a nod toward the private-school uniform, with its bright brass buttons and embroidered patches. A classic navy jacket worn with white jeans and a striped shirt looks crisp and put-together. For a more collegiate feel, consider gray flannel and tweeds in earth tones worn with a mini skirt or denim. Leather belts and shoes with gold details add polish and always look smart.
Bright striped grosgrain silk ribbon never fails to pop. Think of a red and green Gucci watchband, belt or handbag strap or a diagonal yellow and burgundy sash that draws the right kind of attention. Grosgrain can be seen as piping on jackets or trim on dresses and cardigans. It’s cheerful, high-contrast and extra sharp.
5. Cotton Shirts
A crisp cotton button-down shirt in white, blue or pink will elevate any outfit. Solids or vertical stripes take casual dressing up a notch, and they can be worn with everything from khakis to jeans, skirts, slacks and plaids. They look great with a blazer but can also convey a relaxed feel when worn half-tucked and unbuttoned at the collar.
Pearls have always been a hallmark of elegance, sophistication and femininity. Their luster may be subtle, but there’s no way to wear a pearl necklace without feeling upscale and intentionally dressed. Pearls can be prim and proper, but they needn’t be stuffy. For a ladylike take on preppy style, you can’t go wrong with pearls and a cashmere sweater. If you want to modernize pearls, pair them with bright pastels.
7. Tweed, Checks and Plaids
Tweeds, checks and plaids instantly add luxurious texture to any preppy outfit. In the fall, a wool herringbone or Harris tweed jacket looks bookish and speaks to leisurely strolls in the country or coffee off-campus. Tartans and glen plaid can look cozy or streamlined depending on the fit and finish of the fabric.
Whether strong or subtle, these patterns easily coordinate with button-down shirts, sweaters and close-fitting cute tops. In summer, cotton gingham and polka dots always look fresh. Vivid and contrasting weaves can make standout hats and scarves. With their versatility and evergreen appeal, including these patterns in your preppy wardrobe is a sure bet.
8. Tailored Trousers
Preppy style can look effortless, but it’s always intentional. There’s no denying that tailored trousers in wool, twill or khaki are a step up from jeans. Pleated or flat-front trousers look elegant when paired with an ironed button-down shirt, handmade loafers and a belt with gold hardware. They can be slim or slouchy, so long as they’re thoughtfully fitted and accessorized.
9. Novelty Sweaters
A well-made novelty sweater injects a little fun, irony and personality into your wardrobe. Preppy novelty sweaters are often humorous and brightly colored, featuring animals, sailboats and flowers.
The cute and kitsch factors are toned down a bit by arranging designs in orderly rows and patterns for graphic appeal. A novelty sweater says that you don’t take yourself too seriously, but you’d never let yourself go.
Express Yourself With Preppy Style
Today’s preppy styles are youthful, playful and knowing. The look can be sporty and active or literary and cerebral, but it’s never sloppy. The fit and finish are all about fit, tailoring and assertive individuality. The preppy style is never too literal, but it’s always aspirational.
This look is a sophisticated take on tried-and-true staples that enlivens the classics without violating any norms. Headbands, pastels, tennis skirts, polo shirts and boat shoes all have their place in the pantheon of preppy style. Build your wardrobe with highbrow essentials, and then inject your own point of view. Preppy fashion is all about letting your personality shine through.