preppy

Apparently, you’re supposed to know without being told, which is a very preppy attitude indeed.

From The Wall Street Journal ● Jun. 19, 2026

The top look this year, ironically, is “Old Money,” a fashion trend that emphasizes expensive, quality pieces and classic styles — not so much head-to-toe logos, but more tailored blazers, preppy vibes and subdued hues.

From Salon ● Dec. 27, 2024

The crowd in the dining room was a mix of older and younger, but most people were dressed on the preppy side in gingham and Ralph Lauren.

From Slate ● Nov. 2, 2024

In 1987, David Letterman was taping his late-night show in Las Vegas before rowdy audiences of mostly young men in preppy pullovers and muscle shirts — prototypical bros raised on “Porky’s.”

From New York Times ● Jun. 19, 2024

Gone was the preppy athlete of her first three years.

From "Tradition" by Brendan Kiely

I thought of my public-school classmates, buying boat shoes at the mall, as preppies.

From New York Times ● Aug. 5, 2019

Within the teen movie pantheon, he was long the black sheep, unwilling to play by the rules that had schoolyard jocks and trust-fund preppies ensconced at the top of the hierarchy.

From Slate ● Mar. 27, 2019

“It wasn’t like we were a bunch of vapid preppies, but God, we were preppy then.”

From Seattle Times ● Sep. 22, 2018

Light-pink-colored swim shorts have the flashy flair of Sonny Crockett from TV show “Miami Vice,” while pinkish denim harks back to preppies with their fondness for eye-searing trousers to match their Madras cocktails.

From Los Angeles Times ● Apr. 27, 2017

But then, he hadn’t gotten along with preppies or jocks either, or with the school’s administrators.

From "Geeks: How Two Lost Boys Rode the Internet Out of Idaho" by Jon Katz

Both are sometimes remembered, sartorially speaking, for their preppier periods.

From Slate ● Oct. 7, 2022

Hill exuded a young architect vibe, but Alfred’s look was preppier — a navy blue cardigan and vintage Ralph Lauren brown corduroy pants emblazoned with ducks.

From Los Angeles Times ● Oct. 10, 2018

The preppier back-half of the show, representing Mr. Lauren’s Polo label, lacked the same broad appeal, though it was masterfully put together.

From The Wall Street Journal ● Sep. 10, 2018

“So you’re going as a slightly preppier version of yourself?”

From Salon ● Oct. 30, 2014

She writes that oceans are preppier than lakes “because they are natural and uncontrollable.”

From New York Times ● Aug. 29, 2010

As a magazine writer he played the part of the preppiest young man in the club, and ingratiated himself as a in-on-the-joke insider—a power journalist who became a source for power journalists.

From Salon ● May 4, 2023

In its long-sleeve form, the preppiest of summer staples is a convincing alternative to dress shirts and sweaters.

From The Wall Street Journal ● Aug. 25, 2016

He was at Phillips Academy in Andover, Massachusetts, at the same time as John Ellis Bush, scion of America’s preppiest leading family.

From Slate ● Jan. 28, 2015

What does that Scandinavian country have to do with the preppiest of American shoe styles?

From New York Times ● Nov. 23, 2012

It’s funny how it ends up being the straightest, preppiest, most athletic guys who go all out for Gender Bender.

From "Simon vs. the Homo Sapiens Agenda" by Becky Albertalli