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

Richman, “who dressed like a kid that everyone laughed at in high school,” influenced the band’s preppy visual template and Byrne’s clenched singing voice.

From Los Angeles Times ● Jun. 17, 2025

The show formerly starred singer Reneé Rapp, who played the preppy mean girl with a heartwarming coming-out arc, but since Rapp’s departure, the half-hour comedy has fully leaned into the show’s absurdity.

From Salon ● Jan. 19, 2025

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 turn to the others and realize that they’re all just as shaken as I am—even the preppy kid.

From "Dry" by Neal Shusterman and Jarrod Shusterman

“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

Generally civil debates began to break out, with the page’s editors disagreeing about everything from whether preppies would mismatch their socks to the age after which one stops qualifying as a hipster.

From Slate ● Oct. 20, 2015

It was a school largely for people from out of town, preppies who observed the surrounding neighborhood with a voyeuristic curiosity when they weren’t hatching myths about it to scare freshmen.

From "The Other Wes Moore: One Name, Two Fates" by Wes Moore

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