I recently came across a not too old article from the Chicago Tribune titled 'The Modern, Evolving Preppy'. I find it interesting as it reviews the preppy thought process vs. the fashion AND it uses Chicago examples. I have copied the entire article below originally by Christopher Borrelli and published on Dec. 5, 2010. Link here
Who is the North Shore preppy today?
Where do they eat? Do they still use "summer" as a verb? How long do they wait each winter before wearing socks on a (semi)regular basis? This fall Lisa Birnbach released "True Prep," a sequel to "The Official Preppy Handbook," her pioneering 1980 work of WASP anthropology. She came through Chicago on a book tour recently and, as expected, preps across the area emerged from behind their piles of Lilly Pulitzer and lacrosse padding to greet her. We dared not step between a rabid preppy and a Lisa Birnbach. However, now that they've retreated to Glencoe and Lake Forest and life has settled down again for the North Shore preppy, the time felt right to learn about them, study them and find out what has changed in the past 30 years of prep-dom.
The old prep went to prep school; came from old money; was tied to the family (and rarely single and rarely self-sufficient); and was white and Protestant and loath to advertise personal details. Was this still the new prep? Before heading into the bush, I called Birnbach.
"I'm not Margaret Mead," she said, "but I've been among the North Shore prep. I have been welcomed into their habitat as warmly as if I had lived there myself. I found them to be the real deal. They seem less jaded than East Coast preps. Prep is really about family, education and travel, and they excel."
The North Shore prep lives in Wilmette, Winnetka, Glencoe, Lake Forest, Lake Bluff and Kenilworth. They typically hug the coast (preppies like water); on weekends, they can be found jogging along Green Bay Road, Sheridan Road and Western Avenue. Pockets reside within surrounding communities, though there is debate on this. For instance, at prep clothing store Lillie Alexander Ltd. in Lake Forest, a clerk said that Highland Park is not prep. "It's just something you know," she said. She said Highland Park, despite being home to Ravinia (a prep attraction), was "more urban" than Lake Forest, setting of "Ordinary People" (a prep landmark). At Helanders Stationers, Highland Park was said to have too many "new money" families to be prep; while at the Lake Forest Book Store, owner Sue Boucher illustrated the difference:
"Someone was just honking (outside the store), and I kept thinking, 'We don't honk here.' In Highland Park, they honk. Decorum is what it's all about."
That is archetypal prep: subdued and well-to-do and WASP. As Birnbach says, "prep is not about fashion."
Consider Beth Erickson and George Chemers. They are married and live in Highland Park and summer on Nantucket and Martha's Vineyard. But their home is modest. They do not appear to be to the manner born. Nevertheless, they are prep: Chemers believes wearing red (well, Nantucket red) pants is perfectly acceptable in public, though his threshold for not wearing socks is only around 40 degrees. Erickson attended Lake Forest College and regularly turns out for church rummage sales, a popular prep pastime.
"Prep is not about money," said Erickson, who grew up north of Milwaukee and hadn't heard of Nantucket until she read the "Preppy Handbook." "I never took (the book) as a joke, but as a way of carrying yourself. It's a lifestyle."
They are, in a sense, of the generation who got in touch with their prep tendencies through study of the Birnbach classic.
Now in their mid-40s, they are not, as Maggie Crane, of Winnetka, puts it, of a younger generation of preps who "throw around a sense they are a bit better than everyone and don't know (prep) also means impeccable manners." Erickson and Chemers are not prone, for instance, to wearing the ostentatious new Ralph Lauren shirts "with the giant Polo pony horrifying to anyone of a true prep sensibility" — so described by Lance Lawson, whose clothing store, space519, in the 900 Shops on Michigan Avenue, has become a North Shore magnet. They gravitate more to regulation L.L. Bean duck boots.
But there are minor concessions to contemporary living that the North Shore prep has had to make in 2010.
Take Libbi Diane Flynn.
She is 29 and calls herself "a new prep," though at first she comes off as old prep. She summers in Door County, Wis. (a prep retreat), and believes in "owning one nice good-quality sweater instead of 12 crappy ones" and is a member of the Kappa Kappa Gamma sorority and describes herself as a "J.Crew-aholic" and was on the crew team in college and praises prep-goddess Gwyneth Paltrow for being a "modern evolving preppy." She arrived a few minutes late to our meeting, saying she had gone through "a prep emergency," having dropped her pearl earrings down a drain.
Friends call her "Bunny."
Yet Flynn is a WIC (white Irish Catholic) who went to high school in Green Bay. Today's prep — "formerly WASP," says Birnbach — is multicultural. Sort of. The new prep does use Facebook, though discreetly: "Thirty years ago, you didn't know who had a second house because people were more humble with money," Birnbach groaned. "Now everyone knows everything." Flynn herself considers social media a contradiction of authentic prep ways; before friending Birnbach on Facebook, she told the author at a book signing that she would be friending her.
Which is only polite.
That said, Flynn notes that Kim Kardashian went to prep school and she didn't, so Kardashian proves that prep school attendance in itself does not make a prep. She also points out that she is young and single and lives by herself.
"It used to be, you would get your pearls passed down from your grandmother," Flynn said. "But I got my pearls while on vacation in Dubai! And you know what? It's not a scandal."
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Overall I thought it was very well written and did a find job of explaining that the stereotype isn't what 'Preppy' is all about... it's a way of life! :)