Preppy trends at New York Fashion Week SS25

This September, The Michigan Daily’s most stylish writers to New York Fashion Week to seek out the coolest collections and exclusive events. We scoured the Big Apple in search of what’s new in fashion and culture this upcoming spring and summer — this is what we found.

On the first Sunday of New York Fashion Week, a male in tan slacks and a red, white and blue color-blocked shirt caught my eye. I thought he was wearing a preppy designer outfit or a Ralph Lauren Olympic Ceremony kit. I was entirely mistaken — he was actually a preteen returning from Little League, not a stylish, slightly short adult. I had been blinded by fashion trends, influenced by the new wave of preppiness that designers and tastemakers carried to New York Fashion Week for spring and summer 2025.

The Oxford English Dictionary defines preppy, from 1963 on, as “Of clothes, appearance, etc.: typical of or associated with students at (prestigious) prep schools; neat, classic, smart.”

The satirical-turned-standard 1980 book, “The Official Preppy Handbook,” defined East-Coast prep, providing guidelines for existing in the crowd and rules for the style, with staples like collared polos, boat shoes, blazers and khaki tones. Designers like Ralph Lauren and Tommy Hilfiger and retailers like Brooks Brothers (founded in 1818) and J. Crew rose in popularity with the tide of prep.

Prep has roots in tradition and timelessness (rooted in England and New England schools) and rebellion and play (the handbook recommends getting kicked out), which makes it change just a bit with the times. Miu Miu’s Spring and Summer 2024 line brought back Abercrombie-and-Fitch-esque, nearly campy prep looks. When placed separately, the line’s recurring plaid ensembles, loose shorts and fitted blazers have always remained relevant, but saw a serious 2024 revival. 

Prep may have never truly been out, but it’s especially “in” today. Preppy social media microtrends exploded across TikTok and Instagram throughout the 2020s. There was the 2020-2022 “Dark Academia” trend, with uniforms, trenches and dark libraries. There was a 2022-2023 sportswear obsession with pleated skirts and Princess Diana-inspired crewnecks and the 2023 “Office Siren” long hemlines and loafers made hot. Both of these subsets of prep experienced their time in the limelight — peaks in the enduring popularity of prep. 

Consequently, in the past two years, long after Kanye West was mocked for his preppy pink polo, cool streetwear brands adopted preppiness. KITH, Aimee Leon Dore and Rolling Blazers revitalized chunky knits, chinos and slacks, refreshed classic suits and exploded in popularity while creating new, looser silhouettes and an exciting technicolor color scheme. This summer was a high point for prep revival in America: Ralph Lauren outfitted the Summer Olympians and hosted a star-studded fashion show tinted with red, white and blue for Spring and Summer 2025. Willy Chavarria placed a pocket constitution on each seat and celebrated vintage sportswear. 

At New York Men’s Week, two designers took on preppiness in exciting ways. Clara Son built cycling-inspired ensembles with streetwear edge and Sivan created a garden-party aesthetic with genderless suits. Notably, the day was sponsored by Sperry, the (in)famous boat shoe king of preppy footwear. Son took a more modern, if not edgy, take on sports-inspired, smart clothing. But her looks still touched upon the timelessness, neatness and fun (within reason) that comes with prep. 

The sleek cycling looks featured real athletic wear, like hoodies and track pants. But everything was tailored and layered to perfection. The pinks, greens and blues were muted and pastel. There were tweeds, sweaters, slacks and khaki shorts. Prep added warmth and wearability to the looks, which otherwise would’ve been industrial-cool with shiny windbreakers and helmet-shaped headwear. The line built upon playful preppiness of tastemakers like Tyler, The Creator, with loose silhouettes, chunky knits and funky colors. The new iteration of prep is partially ironic, playing up the style’s pretension and having fun with it.

One standout look was a muted coral sweater shirt with matching coral khakis. The draped, chunky wool fragments presented prep-classic colors and textures in an almost streetwear-cool way. An outfit featuring navy shorts and a light pink knit with flowers built a beautiful combination of relaxed and classic prep, masculinity and femininity. Another model wore a straw-like textured jacket with nothing under and simple light slacks. The fit was oversized yet perfectly tailored, with a belt draped across the waist. Textured stitches, a plunging neckline and a bucket hat added a casual edge. An additional standout was a funky-prep monochromatic ensemble in muted lime green featuring long shorts, a button-up, hat and suspenders.

Prep and sportswear’s combination upped the line’s sleekness while making it appear effortless and fun. And the stunning spring color scheme made Clara Son’s collection impossible to turn away from. 

Sivan took on prep with more formal, genderless looks fit for a high-class picnic. The designer’s motto “Interested in functionality and fun, in timelessness over trends,” was embodied in the SS25 collection. Sivan’s pleated skirts, shorts and pants were flowing yet tailored. The color scheme was bright yet naturalistic with soft tans and browns, warm yellows, deep greens and navy blues. Designer Jack Sivan built a versatile, modern prep school uniform for spring and summer days. The designer showed beauty in simplicity with a linen dandelion-toned suit and fedora and a fitted, sleek two-piece navy suit. But the most versatile look was also the most dramatic, a voluminous ecru linen skirt with a matching collared jacket. Classic preppy textures and colors shone through in the collection.

Sivan’s clothing is meant to be worn the way the models styled them on set, with the vintage bicycles, among picnic baskets and green grass. Linen, tailored suits and trench coats were stars of the collection, adding a refined sense of vintage luxury. Sivan was exciting, yet built upon the year’s biggest trends and stuck to classics.

Preppy menswear classics were everywhere in the street: people flexed U.S. Open hats showing their appreciation for the classic preppy sport of tennis, and wore collars and pinstripes. Countless women layered pastel sweaters, buttoned striped button-ups and wandered streets in loafers. The once exclusive prep subculture look has become for all genders, backgrounds and classes, from J. Crew to streetwear to couture — everyone can wear it. But it’s still those same boys in plaid school uniforms and summering in striped button-ups. East Coast prep schoolers will wear the same things they always have, and others will wear, rewear and change up their classic style.

The current iteration of prep may just be lasting. It isn’t based in microtrends, but in the classics, with room to modernize through both legacy and rising star designers.

Daily Arts Writer Kaya Ginsky can be reached at kginsky@umich.edu.

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