Preppy Outfits That Reimagine '80s Style

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 2024—in fact, they don't follow a formula at all. From Hailey Bieber's pantsless take on prep, Fashion Month guests teaming techy running sneakers with tailored suiting, 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, has seen 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, the aesthetic breaks from tradition. At Copenhagen Fashion Week, guests wore Ralph Lauren's classic cable-knit sweaters with 2024's top trending sneakers, Oxford shirting with itty-bitty hot pants and chunky white tube socks.

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 cherry red crew socks are fashion TikTok’s favorite pop of color.

In short, as a fall 2024 trend, the preppy aesthetic has remixed and gone rogue. Today, the style is less about emulating a buttoned-up, aspirational way of living the American Dream and more about expressing your non-prescriptive personal style. That said, there’s no harm in garnering preppy outfit inspo from classic prepsters as jumping-off points before trying the trend yourself—which is why we combed through the recent best street style and curated an edit of preppy fall outfit ideas for you to wear, well, however, you want.

Baggy Suiting With Trendy Sneakers

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

Ralph Lauren Redux

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

Barn Jackets and Boat Shoes

Another aspect of 2024'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 fall 2024's most polarizing shoe trend, a boat shoe, for a playful outfit that 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

As expected for fall, layering outfits play a key role in your rotation. Take a point 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.

Forgo Tailored Trousers

Short suits were all over the Fall 2024 runways, from Chanel and Christian Dior to Michael Kors Collection and Dries Van Noten. Snag a set in dark corporate gray and slip on a pair of burgundy slingback heels—both top fall 2024 color trends—for a fall work outfit that offers a peek into your personality.

A Mad-About-You Plaid Mini

Tap into a prepster dropout spirit with a grunge plaid mini skirt (Chopova Lowena's carabiner styles 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

Again, with fall 2024's interpretation of preppy fashion, there are absolutely zero rules—including wearing contrasting vertical and horizontal stripes in one intriguing, graphic look.

Polo Dress

Preppy polo 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 fall, consider a knit polo dress with knee-high boots and some flash on your wrist in the form of a statement watch.

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.