Always Classic, Always New…Fashion: Preppy/Old School Glamour

When thinking about this post I first thought of doing school uniforms then switched to Preppy as a true total lifestyle as mentioned in Jeffrey’s perfect quote below. It can mean so many things…but I must state that it is timeless qualities in that it adapts itself to “now” and “forever”. Perfect for any wardrobe and every gender….and what better place to find this timeless trend than our favorite shopping venue…Randolph Street Market!

“Classic Preppy is always in fashion because it represents for the most part established codes of civility, great taste, and good manners. Unlike many other fashion trends Preppy never ever goes out of style.” Jeffrey Banks, Author (nenasnote…Designer and so much more!)

Featured in PREPPY CULTIVATING IVY STYLE it is THE book to add to your collection, photo from Tommy Hilfiger.

English school uniforms…

In addition, THE OFFICIAL PREPPY HANDBOOK…published in 1980…it has sold millions of copies and is now a collectors item…pretty much tongue in cheek…I wonder where my copy is??!!

PREPPY AS DEFINED IN MERRIAM-WEBSTER’S DICTIONARY
FIRST KNOWN USE 1880

NOUN
1. a student at or a graduate of a preparatory school
2. a person deemed to dress or behave like a preppy

ADJECTIVE
1. relating to, characteristic of, or being a preppy
2. relating to or being a style of dress characterized especially by classic clothing and neat appearance

I have mentioned many of the looks that I will examine in this post in past articles (check the archive in the RSM Blog), including plaid, trench coats, pearls and so on. Other preppy essentials, the blazer, pleated skirts, button down shirts, loafers, stripe sweaters, Fair Isle sweaters, letter sweaters and jackets, khakis….well you get the picture. What brands do we think of…#1 in my opinion, Ralph Lauren, the King of Preppy; Tommy Hilfiger, absolutely; J. Crew made their name with the look. And if want to back in time….look at movies such as Love Story, Anne Hall with Diane Keaton…promoting the look in her own way, in fact, she continues the look to today, of course the movie, Clueless. Think of Taylor Swift and her enthusiasm for cardigan sweaters, Princess Diana as a “Sloane Ranger”, before her marriage. We can even go back to the rebellious designer, Gabrielle Chanel and her version of Preppy….

Mlle Chanel….

Ralph Lauren…to me THE master of the always stylish and elegant Preppy look…here with his wife, Ricky

A few of examples of the looks of Ralph Lauren…

Duke of Windsor….back in the day…

Ralph Lauren’s interpretation of the look topping it with faux fur…

Some things never change…

Love Story, 1970 movie…

Diane Keaton in the film Annie Hall, 1977…a look she wears to this day as her signature style…something I totally advocate, find your style, stick with it, of course updating through the years!

Clueless 1995 movie

Taylor Swift and her cardigan(s)….

Tommy Hilfiger….

Of course, Diana, Princess of Wales, as a London “Sloane Ranger” before her marriage and with her boys….

A few more examples….

And the modern Preppy….

“Thom Browne, fashion’s most dedicated preppy, took subversion to the extreme in a recent collection, with boys in repp ties, grosgrain jockstraps and ladies-who-lunch bouclé skirt suits—a look that one imagines wouldn’t fly at any country club, except maybe one on Fire Island.” Kareem Rashed, Robb Report, 28 Aug. 2022

Thom Browne…

What then is my point…classics can always fit into our wardrobes, they can be the pure look as in all the years of Ralph Lauren or fit into a more trendy look of Thom Browne. Just adding a strand of pearls to a Fair Isle sweater gives it the classic Preppy look that is Always Classic…Always New and guess what you will find some of these looks to add to your wardrobe at RSM…need I remind you to engage the knowledgeable dealers in conversation, they love to have their brains picked…remember you are seeking the “look” not necessarily the brand…but who doesn’t want to score a vintage Ralph Lauren…show of hands, oops mine just shot up!!!!