Casual, chic Carolyn Bessette-Kennedy style moments to inspire your fall 2023 outfits.
(Contains affiliate links)
Gen Z may not have awareness of her at all but we millennials likely remember the beautiful blonde publicist that married America’s top bachelor, John F. Kennedy, Jr.
Carolyn Bessette-Kennedy was a natural beauty who had an effortless way about her that Vogue and Vanity Fair couldn’t get enough of. And who can blame them? America lacks official royals but we as a nation share a fascination with the Kennedy family to the point where one could fairly argue they’re a version of American royalty. The family’s compound on the New England shores of Cape Cod was a hot spot for photographers hoping for a glimpse into their lives on the Nantucket Sound.
But in the fall, it was the streets of New York City where you’d Carolyn Bessette-Kennedy with some regularity — often with her very GQ husband. Their image was captured by paparazzi and blasted across tabloids with a level of frenzy and interest similar to the of Princess Diana and it speaks of what a different time it really was.
A Voyage to End in Tragedy
It was July 16, 1999 when the famous couple hopped on their private jet — heading to the Kennedy compound for a family wedding. It was to be a rather brief trip with a pitstop in Martha’s Vineyard to crop off Caroline’s sister except en route the disappeared in a storm.
The disappearance of the couple on their voyage to a family wedding captivated the nation as rescue efforts were underway.
I vividly remember vacationing at my Grandmother’s cottage on Lake Michigan as a child where my mom and grandma were devastated and we were so worried for the couple — hoping for the best but preparing for the worst. This was a pre-digital age that would be foreign to Gen Z. There was no social media, no wifi and logging on the internet required a modem.
And in time, plane wreckage was found and it was determined that JFK, Jr. as a young pilot lost control of the aircraft while trying to navigate the turbulent weather. It was a tragic ending to a beloved American couple and one where so many found themselves asking questions of “what if” when processing the news.
Their lives were cut heartbreakingly short and what was meant to be a joyous family event turned into one of great loss.
CAROLYN BESSETTE-KENNEDY STYLE MOMENTS
During her time with us, Caroyln Bessette-Kennedy style moments became a key source of interest for the public and fashion editors alike. Vogue, Vanity Fair and the like frequently featured Carolyn in spreads for style inspiration and still do with some regularity.
In the age of influencer, Kardashian and crop tops — Carolyn Bessett Kennedy style moments are strikingly different. She didn’t chase trends or wear flashy attire to capture the attention of others. Instead? She embraced the simplicity of labels such as Calvin Klein — and was rumored ot have a fling with a CK model who went onto write a book entitled The Other Man following her passing (which feels a bit in poor taste).
She didn’t wear tight, figure hugging silhouettes. Nor did she adorn herself in studs or sequins.
Instead? Carolyn reached for classic black as her tried and true favorite with seasonal pops of camel in the autumn/winter months and shades of ivory.
She was American royalty but also became a symbol of the traditional American style that was so popular in the 90s and is thankfully on the rise, again, today. Everything in her closet feels as relevant now as it did over 20 years ago — and impressive feat, no?
FALL 2023 STYLE PICKS CAROLYN WOULD LOVE
As inch closer and closer to bidding summer farewell, there really couldn’t be a better time to look back at the style of Carolyn Bessette-Kennedy as so many of her best street style moments feature bootcut denim jeans, knee-high boots, lush overcoats and over course a lot of elegant black.
So to help inspire you in making selections on your autumn/winter shopping, peruse standout Carolyn Bessette-Kennedy style moments below and start planning your wardrobe for the chillier months ahead!
Who says black attire is reserved only for goths and mourning? The best Carolyn Bessette-Kennedy style moments proudly feature black – including from head to toe.
Available in Standard, Petite and Plus
When not dressed in black, camel was a popular selection in Carolyn Bessette-Kennedy’s street style and it makes for perfect fall outfit ideas that match the golden brown colors of the season.
Skinny jeans? Not her thing. Carolyn Bessette-Kennedy would be routinely spotted around town in bootcut denim balanced with a blouse, great cote and handbag for a more dressed-down professional look.
Of course we can’t discuss autumn style without addressing the increased need for layers to keep warm. Caroline’s collection of coats is perhaps her most iconic element of her style. She was spotted wearing quite a lot of black classics as well as fun pop of animal print.
A GOOD WHITE SHIRT
Great white shirts have become the uniform of choice for many. They’re versatile and can be both dressed up or down to suit any occasion. There a number of excellent Caroline Bessette-Kennedy style moments that prove she’s on the same page as the rest of us. A good white shirt is an absolute must in any capsule wardrobe.
Available in Camel and White
CLASSIC WORK BAGS
As a busy working woman in the 90s, Carolyn Bessette-Kennedy would be spotted on the sidewalks of New York with black, work bags to house the essentials while on-the-go. Of course her number one choice as a Birkin — but as that’s not a feasible option for everyone… find great alternatives, below!
Available in Black, Camel Brown and Evergreen
NO FUSS FOOTWEAR
When came to footwear, you’ll notice that Carolyn Bessette-Kennedy style didn’t chase trends nor did she go to super high heels with loud colors. Instead she leaned into the classics with black and occasionally brown as her color palette, low height heels and traditional cuts like over-the-knee boots, kitten heals and mules.
Available in Black, Tan/Black and Navy/Black
WANT MORE FALL INSPO?
Join the #DreamSquad:
Sign up for the weekly newsletter and receive exclusive dreamer content you won’t find on DREAMINLACE.com straight in your inbox. Let’s be dreamers, together!
Stay stylish and chase your dreams!