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

Compared to the resort-ready tunics and preppy Reva flats that embodied Tory 1.0 in the 2000s, Tory 2.0 has evolved into a “weirder,” more innovative version of itself.

From Los Angeles Times ● May 14, 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

I said, “I’m okay,” and we crowded onto the ride, shoving past some preppy parents who dragged their whining, disinterested brats alongside them.

From "We Are the Ants" by Shaun David Hutchinson

“My cliquish world consisted of ladies and gents from Manhattan’s exclusive private schools and preppies down from New England boarding schools who played bit-parts on weekends and holidays,” she wrote.

From New York Times ● Oct. 10, 2022

“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

The topic was polarization between cliques in high school — “greasers” vs. jocks and preppies — and how to foster mutual respect.

From Washington Post ● Oct. 17, 2016

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

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

"I go to school at SUNY–Binghamton, and a lot of kids wear them—the preppier, more GQ–style kids."

From Slate ● Jun. 26, 2013

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