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DreaminLace

STYLE + BEAUTY + AMBITION OF THE MODERN WOMAN

Designer Fashion, Fashion

Fall 2023 Outfit Ideas – Courtesy of Carolyn Bessette-Kennedy

August 28, 2023

Casual, chic Carolyn Bessette-Kennedy style moments to inspire your fall 2023 outfits.

(Contains affiliate links)

Carolyn Bessette-Kennedy Style Moments that make for the perfect fall outfit ideas.

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.

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

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!

 

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

BLACK ATTIRE

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.

 

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

SILK CREPE DRESS

Carolyn Bessette-Kennedy Style Inspired Fall Outfit Ideas I LaFayette 148 Crepe Jacket

RESPONSIBLE WOOL CREPE JACKET

Available in Standard, Petite and Plus

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

CAMEL MOMENTS

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.

 

Carolyn Bessette-Kennedy Style Inspired Fall Outfit Ideas I St. John Camel Overcoat

CAMEL WOOL AND CASHMERE BLEND OVERCOAT

Carolyn Bessette-Kennedy inspired fall outfit ideas camel corduroy trousers

CAMEL CORDUROY TROUSERS

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

BOOTCUT DENIM

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.

 
Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

CHIC OVERCOATS

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.

 

Chic overcoat

CLASSIC BLACK OVERCOAT FROM MACY’S

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

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.

 

Carolyn Bessette-Kennedy Style Inspired Outfit Ideas I Calvin Klein Relaxed Twill Collared White Shirt

CALVIN KLEIN RELAXED TWILL SHIRT

Available in Camel and White

Carolyn Bessette-Kennedy Style Lookbook to Inspire Your Fall Outfit Ideas

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!

Carolyn Bessette-Kennedy Inspired Outfit Ideas I Hermes Black Birgin with Gold Hardware

HERMES BIRKIN

Carolyn Bessette-Kennedy Style Inspired fall outfit ideas

FAUX CROCODILE EMBOSSED LEATHER TOTE

Kate Spade large black work bag

KATE SPADE LARGE WORK TOTE

Carolyn Bessette-Kennedy inspired all outfit ideas -- COACH Outlet carry all tote

COACH OUTLET CARRY ALL

Available in Black, Camel Brown and Evergreen

Fall Outfit Ideas I Kate Spade Large Work Tote

KATE SPADE LARGE COMMUTER TOTE

Chic Carolyn Bessette-Kennedy Style Lookbook to inspire fall outfit ideas

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.

Black women slingback pumps that suit Carolyn Bessette-Kennedy style inspired outfits

SLINGBACK PUMPS

Available in Black, Tan/Black and Navy/Black

Carolyn Bessette-Kennedy inspired fall outfit ideas I Valentino flats

PATENT LEATHER BALLET FLATS

Carolyn Bessette-Kennedy style inspired fall outfit ideas I Khaite over-the-knee black boots

KHAITE OVER-THE-KNEE BLACK BOOTS

Vegan leather Stella McCartney studded sole loafer with silver metal hardware chain

VEGAN PATENT LEATHER LOAFER WITH SILVER METAL ACCENTS

Easy Fall 2023 makeup trends to start wearing in your beauty routine, now!

WANT MORE FALL INSPO?

Hop over here to review makeup trends you can easily add to your beauty routine!


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Kelly

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