Classic, Chic, and Always In: The Key Elements of Preppy Style
By: Patricia Mae Olson / Piqued PR
I recently listened to an episode of the Articles of Interest podcast on Ivy League fashion, and I loved how it concluded—over the course of seven episodes—that preppy style is always “in” and classic in America. Through my own podcast, The Preppy Podcast, and countless guest interviews, I’d have to agree.
Preppy is not just a style; it’s a lifestyle. The clothes and accessories you choose help you live out that lifestyle. When you think of preppy, you think of walking the cobblestone streets of Nantucket Island in cozy Nantucket Red knits, you think of shopping on Worth Avenue in colorful printed caftans, you think of Southern sorority girls pledging in their Lilly Pulitzer dresses, you think of recent grads walking around FiDi in their J.Crew blazers, and you think of enjoying a cocktail in a vintage fur passed down from your grandmother.
America made its fashion debut in the mid-20th century with the invention of sportswear—essentially clothing designed for your favorite hobbies… apparel for your lifestyle! Preppy fashion is timeless: classic, colorful, layered, and often passed down through generations. But most of all, it’s lived in!
While preppy has always been a staple of American fashion, it’s certainly having a moment right now. With the release of Kingdom of Prep, a book about the rise (and fall, and rise again) of J.Crew, the resurgence of polo shirts across e-commerce sites, renewed interest in country club sports like golf and the craze of pickleball, plus sightings of Ivy League-inspired ties and other preppy nods on recent runways, now is the perfect time to add some classic preppy pieces into your wardrobe.
Here are some of my favorites to get you started:
- Cashmere Sweater – Perfect to wear alone with a beautiful piece of jewelry, or layer under a blazer or tuck into a skirt. I prefer cream or tan, but black is also great. You can find affordable options on Quince $50 Cashmere Sweater or luxe versions from Alice Walk Luxe Cashmere Sweater.
- Ballet Flats – Not only comfortable, but always chic. My favorites are my Chanels, but Lalisa or French Sole offer excellent alternatives.
- Tweed Blazer or Lady Jacket – I wear these all the time because they’re so versatile. Whether for work events, date nights, or travel, they work with any occasion depending on how you style them. My go-to stores are Tuckernuck Tweed Lady Jacket and J.Crew Blazer Jacket.
- Simple Leather (or Faux) Bag – Look for one without logos all over it, ideally a size between a clutch and a tote for both day and night. I love the genuine Italian leather bags from Colores Collective in classic designer shapes, and Milly Kate has a beautiful cream one.
- Everyday Jewelry – I mean jewelry that you wear without thinking and that becomes your signature. For me, it’s a pinky signet ring with my wedding crest, but it could be a little diamond stud, a pearl cluster earring, a gold pendant necklace, or even a diamond tennis bracelet.
I hope these recommendations help you build a preppy wardrobe that will never go out of fashion.
Whether you’re adding a new piece to your wardrobe or refreshing your style, these timeless preppy essentials will always have a place in your closet. Stay true to the preppy lifestyle—classic, chic, and always in season.
-Patricia Mae Olson
About the Author:
Patricia Mae Olson is the owner of Piqued PR (piquedpr.com), a public relations firm working with lifestyle brands. She is the host of The Preppy Podcast (thepreppypodcast.com), where each Tuesday she interviews the brands, businesses, and influencers keeping the modern preppy lifestyle alive. You can shop all things preppy from her podcast on Shop Preppy (shoppreppy.com), carefully curated by Patricia with finds from the brands she interviews. Follow along with her on social media @patricia_mae_olson and on her blog patriciamaeolson.com and thepreppypodcast.com.
Photos provided by: Patricia Mae Olson
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4 responses to “Classic, Chic, and Always In: The Key Elements of Preppy Style”
Love that preppy is making a return, although I never stopped dressing preppy.
Thanks for sharing the links. I’ll be adding those cashmere sweaters to my birthday list!
Preppy is such a classic style to wear no matter what your age.
Who doesn’t love a good cashmere sweater or navy blazer?!