These days, all the fashion girlies want is to look clean, polished, and expensive but not overtly so—and designers have taken note. Brands like The Row, Theory, Khaite, Uniqlo, and more have exploded in popularity, and the aesthetic they’re peddling is, in essence, that of Carolyn Bessette Kennedy.
Carolyn remains the ultimate ’90s style icon—Hulu basically made an entire series about it in its new show Love Story. (Technically, it’s about her relationship with John F. Kennedy Jr., but let’s be honest: We’re all also watching for the clothes.) Several of her ’fits have been inducted into the fashion hall of fame, but her catalog doesn’t end there—far from it.
And all of those underrated ’fits are waiting for you, right ahead. Keep scrolling for a much-needed revisit of Carolyn’s most iconic ’90s outfits that will literally never go out of style.
Khaki Skirt and Prada Bag
Carolyn Bessette Kennedy and JFK. Jr’s relationship was considered a whirlwind romance, but the true love story lies between Carolyn and her beloved 1995 Prada. The bag tops my shopping list to this day, and her choice to style it with a khaki pencil skirt and contrasting boots, likewise, still holds up.
Tortoise Shell, Leather, and Fur
Her simplest outfit would inevitably become her most famous, pinned to every moodboard across the internet. And there’s a lesson to be learned here: The combination of leather, fur, and tortoise shell is never not chic.
A Flippy Floral Dress
Rest in peace, CBK. You would have loved Reformation. Consider this floral sun dress a reminder that her style extends far beyond black top coats and kick-flare jeans.
A Strapless LBD and Opera Gloves
CBK walked so today’s fashion girls could run...in luxe velvet opera gloves. Styled with a strapless pencil dress, she was the picture of elegance.
Red Tweed
Though her legacy is mostly rooted in neutrals, Carolyn did color just as well. This crimson tweed number is truly the ultimate statement coat.
Creamy Column Dress
Always ahead of the curve, she sported the beloved column dress trend all the way back in 1998. Hers came with a posh twist in ivory tweed versus classic black.
Loafers and Kick-Flares
This photo can singlehandedly be credited for the return of flare jeans. Paired with loafers and a wool coat, this look stresses just how elevated the throwback denim style can actually look.
Ruffled Skirt and Button-Down
This look is the perfect combination of formal and professional: a crisp button-down on top and a ruffled maxi skirt on the bottom. Take notes for your next office party.
A Simple Tank and Jeans
Here, CBK embodied a simple truth I’ve known for a while now: A high-neck tank top will always look cooler than a low-cut style. Finished with medium-washed jeans and strappy gold sandals, the vibe is utter perfection.
Kelsey (she/her) is a freelance digital fashion editor and writer with a knack for turning top-performing content into top-selling content. She has extensive experience in editorial and e-commerce strategy, having worked in both divisions during her years at Seventeen and Bustle. With more than a decade of experience in digital media, she also offers creative and social media consulting, as well as copywriting services. She enjoys cheeseburgers, traveling, and vintage hauls. Follow her on Instagram at @klstieg.
