preppy

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

“I viewed the brand for preppy styles geared to an older generation,” said Lavinia Gabriele, a 26-year-old New Yorker, who works in retail.

From The Wall Street Journal ● Dec. 22, 2025

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

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

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

From Los Angeles Times ● Aug. 24, 2026

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

From Slate ● Oct. 7, 2022

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

Of course preppier sorts might want to try Swifty’s, on Lexington Avenue just north of 72nd Street, for citified country-club food in an atmosphere that recalls Salinger.

From New York Times ● Apr. 7, 2011

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