Why preppy style just won't quit

Here's everything you need to know about nailing the Ivy League look

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Orin Carlin

Content Writer

Tania Leslau

Fashion features writer

Updated: March 20, 2025Mar 20, 2025, 3:04 PM GMT

Some fashion trends occupy a fleeting existence, whereas others boast comeback after comeback.

The preppy renaissance is testament to the Ivy League-inspired aesthetic's everlasting appeal.

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And who could possibly object? Looking like you belong in a vintage Ralph Lauren advert is honestly such a vibe…

What is preppy style?

The term derives from "preparatory", associated with the private university-preparatory schools attended by Ivy League aspirants. It embodies a subculture, upper-class students with a taste for exclusivity and old-school elegance.

Miu Miu SS24 model wearing navy blazer, shirt and polo top combo — Miu Miu SS24

The trend's origins are rooted in the early 1900s. For menswear, the preppy look has much in common with the "Ivy" style, taking its name from the group of prestigious northeastern US universities.

"It's giving grown-up Gossip Girl mixed with country club chic, and we're into it."

The quintessential Ivy look had much to do with elite, aspirational pastimes. A fusion of sportswear and everyday apparel – think golf, polo, cricket, tennis, rugby and the like – evolved over time into what we now think of as preppy.

By the time the 1980s rolled around, the style had flourished, owing much to the publication of 'The Official Preppy Handbook'. The satiric guide gently ridiculed the subculture, but many unironically fell hard for the aesthetic, especially when labels such as Lacoste, Ralph Lauren and Tommy Hilfiger cottoned on and catered preppy to the masses.

7 ways to nail preppy style like a pro:

1/7

Pleats Please

Pleated skirts are you one-way ticket to nailing preppy-chic. Pair yours with white ankle socks and a tee for a tenniscore-inspired look, or layer over trousers for a true cool-girl moment.

OG fashion icon Cher Horowitz was a fierce advocate for the pleated mini. Extra points awarded for plaid.

2/7

Loafer Love

Complete your look with a pair of chunky loafers that radiate school-girl nostaglia. Whether adorned with buckles, embellishments or extra chunky soles, these kicks are thoroughly Gossip Girl-coded.

3/7

Jumper Draping

The key to looking as if you've just strolled out of your local country club? A cashmere knit coolly slung across your shoulders. We'd pair ours with a blazer and pinstripe trousers for a prep-tastic ensemble.

4/7

Cricket Charisma

Preppy specialist Ralph Lauren was one of the OG brands to pioneer this particular aesthetic. The humble cricket jumper has experienced a comeback, now worn by both European It-girls and grandpas on the golf course.

5/7

Knee-High Nostalgia

Take heed from Miu Miu's 2024 runways and pair some knee-high socks with a flippy mini skirt to create a polished, preppy look. An aesthetic beloved by Emma Corrin, EmRata and FKA Twigs, this sock-skirt combination is here to stay.

6/7

Ballet Babe

Ballet pumps - the hero piece of 2024. Yet, it seems the flats are already taking SS25 by storm, continuing their reign into the new season. Charming and feminine in equal measure, the shoes can conjure up in-school style to perfection when teamed with thick socks and a blazer combo.

7/7

Hairband Brilliance

The headband. It's giving Sloane Ranger, and we're here for it. Team with a string of pearls and glossy loafers for maximum impact.

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