Happy Thursday, ladies! Today, I’m sharing 5 classic preppy outfits. Preppy style fashion for women was epitomized by First Lady Jackie Kennedy, who not only embraced classic style but preppy style. Jackie was known to wear brightly patterned sheath dresses from Lilly Pulitizer and catapulted Jack Rogers sandals into the fashion stratosphere.
on a trip to Italy, Jackie spied a pair of sandals she loved. when she returned to the States, she asked shoe cobbler Jack Rogers to make her a pair. The rest is history.
Women who love preppy style embrace low heels tailored skirt suits, wrap dresses, sheath dresses, shirtdresses, silk or cotton blouses, a-line skirts, and chinos.
While preppy style is unique to America, it has been embraced by other continents and cultures. When Princess Diana stepped onto the fashion scene as a Sloan Ranger, her outfits embodied floral denim and skirts, gingham pants, and bright colors.
Preppy style retailers include Talbots, J.Crew, Ralph Lauren, Orvis, Eddie Bauer, and Lacoste, to name a few.
The Summary
Today, I’m sharing 5 classic preppy outfits.
The outfits feature a variety of different looks and items, all of which you can mix and match to create something you love
For each inspiration outfit, I’ve built a new one from the spring lines of a variety of different retailers
Everything is shoppable via text- and image-widgets
5 Classic Preppy Outfits
1. Blazer
This outfit is great for cool-to-mild weather travel. I have a classic white button-up and a sweater that can be worn alone.
Blazers are probably at the top of the preppy style list. Especially when it’s wool, twill, or tweed with a plaid, houndstooth, or herringbone pattern.
But it doesn’t end there. the shape of a blazer, in general, fits with the preppy aesthetic. Remember, we’re talking about a style that evolved from the prep school uniforms of the northeastern US. So, blazers and loafers were/are central to the look.
Similar outfit
Board: The Notched One Button Blazer (Ann Taylor) | Boyfriend Shirt (Talbots) | Everyday Relaxed Jeans (Talbots) | Loraine Bit Loafer (Sam Edelman) | Cable Knit V-Neck Sweater (Talbots)
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2. Polo
There are a lot of ways to dress preppy: from a tweed blazer and jeans to penny loafers and plaid pants, the combinations are endless.
I have played with and continue to play with that base look by mixing and matching color and pattern combinations. Today, we’ve taken a classic combination: a polo shirt, plaid pants, and sneakers and turned it on its head just a bit.
Similar Outfit
Board: Perfect Crops (Talbots) | Cotton Petit Piqué Polo (Lacoste) | Blazer Low Platform Sneaker (Nike)
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3. White Denim
You cannot go wrong with white denim, really. It’s a staple of the classic, preppy wardrobe. And I always wear mine come Spring & Summer.
I’ve paired my jeans with a blazer and added a little flare with a fun graphic tee.
Similar Outfit
Board: High-Waist Straight-Leg Jeans (Talbots) | The Relaxed Double Breasted Long Blazer (Ann Taylor) | Zebra Stripe Tee (Chico’s) | Doran Strappy Sandal (Sam Edelman)
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4. Leather Tote
What are some preppy essentials I keep in my closet? A leather tote, button-down shirts, denim (skirt or jeans), and a cardigan.
Throw in a belt, and that makes six. Even if you’re not a fan of belts, the above list will give your wardrobe mix-and-match capabilities ’til the cows come home. The options are endless.
White and brown is a classic color combo that I love to wear all summer long. Sneak some blue into the mix if you want to amp up the preppy volume.
Similar Outfit
Board: Denim A-Line Skirt (Talbots) | Stripe Oversized Shirt (Ann Taylor) | Dean Pointy Toe Flat (Linea Paolo) | Textured Fringe Open Front Cardigan (Talbots) | Marlowe Leather Hobo (J.McLaughlin)
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5. Striped Shirt
Stripes are a staple in my closet, but it’s fun to mix the look up a bit with pattern. And I’m certain you’ve noticed pattern mixing is quite on-trend these days.
Love mustard color—it is quite versatile, and goes well with blue, orange, and certain shades of green.
Board: Lakeside Stripe Crewneck Top (Alex Mill) | Ribbed Wedge V-Neck Cardigan (Ann Taylor) | Haidee Gladiator Sandal (Born) | Ivy Pants (J.McLaughlin)
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In Case You Missed It
This morning, Kelly shared some of her favorite spring picks. Click the title or image below to read the article.
Petite Picks for Spring
About The Author
YAAYY!! for all things preppy. This has always been my most favorite style for me, even though I wandered from it for many years. Not anymore. I’ve declared PREPPY and wearing it proudly! And, who can forget Ali McGraw in Love Story. Such swoon- worthy preppy outfits in each scene. Like you, Beth, I was mesmerized by the outfits in this movie.
And you look wonderful in all of your preppy outfits, Beth!
Yay for preppy style. It will always be my first choice! And Ali McGraw in Love Story is what started my love affair with all things preppy.
Always has been my favorite style,it’s one reason I started following you.
You have great fashion sense and I love the way you stay on trend while still managing to be classy AND classic.
Nice to have a look back at these great outfits.
Happy St. Patrick’s Day tomorrow ☘
Thanks, Georia Peach! I always love to hear from you!
Love Preppy too! And you do it very well! Love the outfits you put together and the ensemble pieces you highlight. Bravo!
Jack Rogers sandals: I actually prefer Palm Beach brand (similar styling). Here’s an interesting story about Jackie’s iconic sandal:
https://artofstylengrace.com/tale-iconic-summer-sandal/
Look forward to seeing Oscar — Happy St. Patrick’s Day!
Hi Carolina Girl!
Yes, I’ve shared that story many times here on the blog. Just love fashion history.