preppy

At peak times on Saturday, just before sunset, the narrow two-way street to Duryea’s is filled with cars as high-heeled and preppy patrons walk along the sloped grassy shoulder of the road.

From The Wall Street Journal ● Aug. 24, 2026

Describing her own music as “whimsical,” she typically opts for a preppy, ’90s-inspired look to complete the vibe and identifies as a miniskirt warrior.

From Los Angeles Times ● Apr. 3, 2026

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

Diego howled—earning us glares from the preppy parents who probably presumed we were drunk—and the wave of bad music continued to assault our ears as Creed blurred into Nickelback.

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

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

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

Should I have dressed preppier, like the quick-reflexed, collegiate fencing villains in the movies?

From Los Angeles Times ● Aug. 24, 2026

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

Avocado and squid crostini were washed down by Champagne and vodka by the stylish crowd, who wore a range of streetwear and preppier outfits, reflecting Mr. Snyder’s go-to aesthetic.

From New York Times ● Jul. 12, 2017

“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

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