These Unconventional Preppy Outfits Rewrite the Style Rules

Back in the 1980s, a prepster's uniform was cookie-cutter precise. Sweaters were slung over shoulders, and button-down shirts had their collars popped. Plaids came in every possible pastel, like seafoam, salmon, and butter yellows. But preppy outfits no longer follow the same formula in 2025—in fact, they don't follow rules at all. From Hailey Bieber's pantsless take on prep, Fashion Month guests wearing their schoolgirl blazers with high-tech running sneakers, and Miu Miu rebranding boat shoes (of all things) as a quirky-cool, downtown staple, fashion has officially tossed The Official Preppy Handbook out the window.

Sure, traces of classic '80s prep are still in play. Shopping platform and data aggregate Lyst's 2024 Q3 index reports that Ralph Lauren, a brand instrumental in crafting the decade's collegiate codes, saw a 151 percent spike and ranks at number 14 for fashion's hottest brands, eclipsing cult favorites minimalists like Toteme. For non-retail nerds, that's a significant surge for a brand that previously wasn't on the bingo card at all.

When the brand's classic wares fall into the hands of fashion folks, that's when the aesthetic breaks from tradition. At Copenhagen Fashion Week, for one, showgoers wore Ralph Lauren's classic cable-knit sweaters with everything from 2025's top trending sneakers, uniform-issued crew socks, and itty-bitty hot pants.

Speaking of socks, they have become a crucial styling touch for the nouveau-prep look. Bieber, Bella Hadid, and Zoë Kravitz rarely leave the house without tall tube socks peering over their best loafers. Sheer knee-highs are the street style set’s favorite homage to their schoolgirl days, and bright red ankle socks are fashion TikTok’s favorite pop of color.

As a spring 2025 trend, the preppy aesthetic has been remixed and even gone a bit rogue—in the best way possible. Today, the style is less about emulating a buttoned-up Ivy leaguer and more about expressing your personal style without a prescription.

But there's no harm in drawing inspiration from classic preppy styles before experimenting on your own. That's why we've combed through recent street style and curated a selection of preppy spring outfit ideas for you to wear, well, however you want.

Outside the Crayon Box

Milan Fashion Week's s corporate-core street style—a trend that takes office dress codes outside of cubicles—brought polish and professionalism to the city streets. This showgoer chose shades of burgundy and chocolate brown for her business best, which tied into another of-the-moment look full of unexpected color combinations with a rewarding style payoff.

Baggy Suiting With Trendy Sneakers

Throw on Adidas's Sambas alternative, the SL 72, with an eye-catching, oversized blazer and a pair of baggy trousers instead of an expected loafer or pump. A favorite among the Hadid sisters, Emily Ratajkowski and Dakota Johnson, the retro-preppy sneaker adds the right amount of sporty touch to suiting.

Ralph Lauren Redux

Here is a prime example of how the fashion crowd pushes the preppy Ralph Lauren brand beyond its signature style. This combination of a Ralph Lauren multi-stripe button-down shirt, pinstripe shorts, cap-toe pumps, and chunky legwarmers is so whacky that it works.

Barn Jackets and Boat Shoes

Another aspect of 2025's preppy spirit is a nod to English country style—namely, the omnipresent barn jacket trend that makes the fashion set look ready for farm chores. Mix in fashion's most recent polarizing shoe trend, a boat shoe, for a playful outfit that ties into the fisherman aesthetic and works both at sea and on land.

A Wild Button-Down

When crisp white or soft baby blue feels too boring, try a button-down shirt done in a graphic animal print. A flirty fringe skirt and a bright shoe will tie the wild look together.

A Quirky Sweater Vest

Layering outfits play a key role in this spring's fashion—especially for the transitional season. Take cuest from this eccentric dresser with a striped button-down worn under a graphic sweater vest. A corduroy skirt and kitten heels will finish it off nicely.

Forgo Tailored Trousers

Preppy outfits featuring short suits were all over the Spring 2025 runways, from Chanel and Carolina Herrera to Michael Kors Collection and Dries Van Noten. Snag a set in dark corporate gray and slip on a pair of burgundy slingback heels for a work outfit that offers a peek into your personality.

A Mad-About-You Plaid Mini

Tap into the dropout spirit with a grunge plaid mini skirt (Chopova Lowena's carabiner skirts, as pictured above, have a rabid cult following among fashion folks) and a worn-in leather bomber jacket. Sensible Mary Jane flats offer a grounding final touch to the too-cool-for-school look.

Pattern Clashing

Contrary to your popular opinion, wearing contrasting vertical and horizontal stripes isn't a faux pas, and according to Spring 2025's interpretation of preppy fashion, there are absolutely zero rules. A great trench—like Sézane's Clyde trench coat—and socks in the tart cherry red color trend will tie the graphic look together.

Polo Dress

Preppy polo and rugby shirts have undergone a rebrand as of late, with brands like Miu Miu, Dries Van Noten, and Loewe showing the sporty staple as a versatile top for date-night dinners or drinks with friends. For spring, consider a thick polo dress with knee-high boots and a statement watch that's anything but demure.

Shift Into Sports Mode

Yes, technical, running-ready sneakers are an unexpected option for striped shirting and an A-line mini skirt—but that's why the choice works (see TikTok's 'wrong shoe theory'). Plus, you'll rarely regret opting for a comfort-first shoe.

Schoolgirl Stockings

A pair of knee-high socks (yes, like the ones in your prep school uniform) will level up even the most put-together loafer outfits. Think of the hosiery as a more exciting alternative to tights.