It is interesting and quite telling if I am being honest, that any Carolyn Bessette-Kenney inspired wardrobe that I post are the ones that get the most requests to update each season. For those of you who have asked, this is my way of updating it for you.
When I set up this site way back in 2013, I didn’t know the ins and outs or the best practices for setting up a site.
I went by what I saw other people doing and what was suggested which means that I opted to have the dates put in the URLs of my posts, which is definitely not recommended now.
But since I don’t have an IT person and can’t afford one, I am definitely not going to try to changing that option myself and risk breaking my site. So the dates stay.
This means that I can’t go back to old posts to update them and republish as new because the URL date will still show it as old.
I actually have to write entirely new posts every season if I want an update.
So here we go.
We are now going to talk about one of the most iconic fashion muses to this day, even though we only have a select number of photos from her and most are just candid ones of her living her life.
So the question is:
Why is Carolyn Bessette-Kennedy’s Style so Iconic?
Carolyn Bessette-Kennedy’s style has endured the test of time and remains iconic because of its effortless simplicity, understated luxury, and sophisticated minimalism.
While many fashion icons are known for bold, trend-setting looks, Carolyn’s approach was remarkably different because she mastered the art of pared-down elegance, proving that simplicity can be just as captivating, and perhaps even more relatable than the most bold fashion statements.
Did you know that she never actually gave interviews? She just let her clothes do the talking which is why she is one of the most revered icons to this day.
She also never accepted brands gifting her things so what she wore were pieces that she sought out for herself that she loved.
We all love authenticity like that.
Today’s focus is going to be more on her winter looks because this woman loved a good coat. So much so that three of her coats are going up for auction at Sotheby’s at the end of the month.
Most notably her vintage animal print coat that is estimated to bring in 20-30K but I feel it will be substantially more. If I was a rich person, this would be something that I would try to collect.
How to Replicate Carolyn Bessette-Kennedy’s Wardrobe
Turtleneck | Dark Jeans | Brown Boots | Headband | Black Tee | Black Handbag | Animal Print Coat | Black Slip Skirt | Strappy Heel | White Long Sleeve | Loafers | Green Clutch | Black tailored Coat | Black Sunglasses | Tan Skirt | Black Pants | Sweater | Faux Fur Scarf | Black Low Boots | Blazer | Gold bag | White Button Up | Black Clutch | Camel Coat | Snake Print Heels | Light Jeans | Mary Janes | Brown Sunglasses | Mermaid Skirt | Black High Boots | Scarf | Large Tote | Black Teddy Coat | Cords
Replicating CBK’s style is generally the same process that I go through when I am building capsule wardrobes, and I am secondhand shopping.
It is like a guideline for what kinds of pieces to seek out that are timeless, classic, and will last forever.
It is kind of funny, because when I was looking up Carolyn Bessette on Pinterest there was a mixture of modern photos from other people and I had to keep zooming in to make certain it wasn’t her because all of the outfits were so timeless that they looked just as stylish today as they did in the 90s.
To me that is the definition of great style. Almost 30 years later and everything still looks so modern.
I also want to point out that CBK lived in a New York apartment and JFK jr’s assistant from that time has talked about in her book Fairy Tale Interrupted that they had small regular-sized closets.
This means that her wardrobe was also small which is why we saw her rewearing the same pieces season after season.
Even her eveningwear which seemed to have the most variation, was mixed and matched for different looks.
Her wardrobe was filled with luxurious materials like cashmere, silk, leather, and wool, yet she wore them in the most understated way possible.
There were no logos, bold labels, or flashy details, just quiet elegance.
This approach has become known today as “quiet luxury” or “stealth wealth,” a style that favours discreet elegance over in-your-face displays of wealth.
Carolyn exemplified this concept long before it became a popular term, and her style continues to influence the way many people approach fashion today.
Simplicity in Outerwear: The Power of a Great Coat
She was a coat person. I get it because I am a coat person. A beautiful coat was a cornerstone of Carolyn’s winter style, with long, tailored wool coats being a favourite.
Her coats were always classic, usually single or double-breasted, and typically in neutral shades like black, camel, and grey.
You could even go with navy, chocolate brown, or olive green as those are considered modern neutrals.
Style Choices: Choose a tailored wool coat with clean lines and minimal embellishments. Carolyn’s coats often had structured shoulders and a slightly oversized fit, allowing for a relaxed yet refined silhouette. A black or camel coat will become a versatile staple, pairing seamlessly with everything from jeans to formal attire.
Quality Fabrics: Invest in high-quality materials like wool, cashmere, or a wool blend. These fabrics drape beautifully and provide the warmth needed in winter, all while offering a polished appearance that enhances any ensemble.
BUT, even Carolyn broke from her norm and wore a coat that seemed to be opposite of how she dressed. The vintage animal print coat which is up for auction is one of her most famous and notable looks.
It worked because she wore what she was naturally drawn to, not what was trendy.
When shopping for coats, make sure to search for these secondhand first because the amount of beautiful wool and cashmere coats on the secondhand and vintage market right now is huge.
White L/S | Black Coat | Dark Jeans | Faux Fur Scarf | Black Boots | Sunglasses | Headband | Turtleneck | Light Jeans | Animal Print Coat | Knit Scarf | Green Clutch
Neutrals Done Right: Building a Timeless Palette
Carolyn’s winter wardrobe leaned heavily on a neutral colour palette, which allowed her pieces to mix and match effortlessly while maintaining a clean and cohesive look. In her winter style, she leaned on blacks, greys, beiges, and whites which she layered thoughtfully for depth and interest.
Choosing the Right Shades: Start with black and grey as base colours and use beige, camel, or off-white for accent tones. Carolyn’s colour palette had a calming effect, adding an aura of sophistication while letting the shapes and textures of her clothes stand out.
Monochromatic Looks: Try embracing monochrome by pairing similar tones in a single outfit. A head-to-toe black or grey ensemble can look incredibly chic, especially in winter. She often layered various shades of grey or black in different textures, creating depth without straying from her minimalist roots.
And as a former Calvin Klein exec she had this look nailed down.
Turtleneck | Cords | Tote | Loafers | Sunglasses | Skirt | Coat | Boots | Clutch
The Art of Layering
As someone who loves to layer, I admire the way that she was a master of it. Always choosing pieces that worked together to provide warmth without appearing bulky.
Her layering wasn’t about adding pieces for show; it was functional, yet it managed to look effortlessly sophisticated.
Essentials for Layering: Start with a fitted turtleneck or cashmere sweater as a base layer. Carolyn often used turtlenecks as an anchor piece, which added elegance and warmth. A high-quality turtleneck in black, white, or grey is versatile enough to pair with various outer layers.
Mixing Textures: Layer wool with silk or cashmere to create depth. She often wore fitted sweaters under her long coats, creating a streamlined look. Incorporate fine knitwear, smooth silks, or delicate wools under more substantial wool or cashmere coats for a layered effect that looks intentional rather than bulky.
To modernized the look I would opt for sweaters in varying silhouettes in order to mix oversized and fitted to build different looks.
Jeans: Namely Levi’s
Carolyn Bessette-Kennedy was known to wear Levi’s jeans, particularly styles that were straight or slightly flared, which suited her minimalist aesthetic. The Levi’s 517, a classic bootcut jean, is one of the styles she was often associated with.
The 517’s are slim fit through the thigh and subtly flare at the hem complementing her style. As it offered a refined yet casual look that she could easily pair with basics like turtlenecks, blazers, and simple button-downs.
The Levi’s 517 has become part of her signature look because it aligns with her love for clean lines and understated, quality pieces, making it an ideal choice for those looking to replicate her effortless, classic style.
We can find a huge selection of vintage Levi’s 517s on the secondhand market so grab a pair and embrace your inner CBK.
Turtleneck | Light Jeans | Black Coat | Snake Print Heels | Handbag | Button Up | Camel Coat | Dark Jeans | Knit Scarf | Tote | Black Boots | Sunglasses
Embrace Tailored Trousers
In the winter, she often swapped skirts for tailored trousers that offered warmth and sophistication, unless of course it was eveningwear.
She favoured slim-fit, high-waisted trousers that elongated her frame and added polish to her outfits, which often had a boot cut or small flare.
Her trousers were typically in black or grey, reflecting her love of neutrals and allowing for versatile pairing with other pieces.
Styling Tips: Look for trousers that have a straight-leg cut or small boot cut. Modern looks could be a wider straight leg, or a kick flare.
A cropped kick flare is good for those of us that are shorter because the will hit the angle with a gentle flare and look great over boots.
Pair them with a slim turtleneck or a cashmere sweater, tuck in your top to highlight your waistline.
Fabric Matters: Opt for trousers in wool or wool-blend fabrics to stay warm. Carolyn’s pants always had a polished yet no fuss look.
Trousers today are less office look and more everyday wear so it will be easy to find a pair that suits your preferences.
Knitwear and Cashmere Staples
Her winter dressing often revolved around high-quality knitwear. She wore simple cashmere sweaters and turtlenecks that she could layer under coats or wear on their own, offering a refined look without added bulk.
Essential Pieces: Invest in neutral-toned cashmere or wool sweaters, especially turtlenecks in black, grey, or cream. A fine-knit black or grey cashmere sweater can be worn repeatedly, making it the epitome of cost-per-wear value, and we all know I love a good cpw situation.
Silhouette and Fit: She preferred fitted knitwear that could be easily layered, as they enhanced the streamlined look she favoured.
The goal is to achieve a smooth, fitted silhouette that doesn’t add bulk when worn under coats or blazers.
Sweater | Skirt | Boots | Handbag | T-shirt | Cords | Blazer | Sunglasses | Mary Janes
Understated Footwear: Simple and Sophisticated
Carolyn’s footwear was understated yet elegant. She typically opted for classic black leather ankle boots or loafers, styles that were practical but refined.
Her footwear choices were always versatile, suitable for both casual and formal occasions, and never detracted from her overall look.
Ankle Boots: Look for sleek black leather ankle boots with a low to moderate heel. Avoid heavy embellishments and choose a pointed or square toe for a timeless look.
Loafers and Flats: For less severe winter weather, consider black leather loafers or ballet flats. These shoes maintain a classic silhouette and blend seamlessly with the rest of the outfit.
Choose high-quality leather to keep the look polished, and pair them with wool trousers or jeans for a relaxed, chic appearance.
Minimalist Accessories
Jewellery: Often she didn’t even wear jewellery and her accessory of choice was sunglasses, or a red lip. But when she did, she chose simple jewellery, such as small gold or silver hoops, a delicate chain necklace, or a classic watch.
These details add just the right touch of elegance without drawing too much attention.
Scarves and Gloves: Carolyn often wore slim wool or cashmere scarves in black or grey when needed. Opt for neutral tones that match or complement your coat. Black leather gloves also work well with her style, adding a refined touch without compromising functionality.
Handbags: Carolyn Bessette-Kennedy’s handbag collection was meticulously curated, much like her wardrobe. Her choices reflected her minimalist, understated aesthetic, favouring classic, timeless designs over trendy pieces.
Two notable bags were a Hermes Kelly bag, and her Prada tote. Which are expensive bags, obviously one way more than the other, so in this wardrobe I went with a similar vibe in much more affordable options like the Fendi tote, and Ferragamo Handbag.
Tip: Ferragamo and Furla are both underrated designer bag options. They are both fabulous, well made and come in a huge variety of styles that have the same vibes as much more expensive varieties.
When it came to hats, you would often see her wear a knit hat or other beanie that you would later see her holding even when she wore eveningwear.
Practicality all the way.
Button up | Skirt | Gold Bag | Heels | Turtleneck | Trousers | Coat | Tote | Boots
The Carolyn Bessette Kennedy Wardrobe Checklist
- Long Tailored Coat
- Slim Fit Turtleneck
- White Button Up
- Straight or Boot Cut Trousers
- Levi’s 517s
- Cords
- Slip Skirt or Slip Dress
- Classic Knit Sweaters
- Sleek Black Ankle Boots
- Minimalist Loafers or Ballet Flats
- Structured Handbag
- Wool or Cashmere Scarf
- Sleek Sunglasses
Carolyn Bessette-Kennedy’s style is famous because it captures a sense of timeless elegance that remains relevant across decades.
She embodied the concept of “less is more,” before we even talked about that term, demonstrating that quality, simplicity, and confidence are the real hallmarks of sophisticated style.
She continues to inspire because her aesthetic offers a refreshing antidote to an ever-faster fashion world, reminding us that sometimes, the most powerful style statements are the quietest ones.
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Great post, as usual ! Each time you talk of a classic turtleneck it makes me want to buy one, but I have a large chest and it looks awful. Any tips on how to pull off the clean turtleneck look for large chests?
I think turtlenecks look fabulous on big busts, but ultimately you have to be comfortable because if you aren’t, it will show. But my tips would be to first wear a well fitting bra. That one is key. Then stick to darker colours, and avoid prints and ribbing. Look for a thin, sleek knit that fits your shape well. You don’t want excessive fabric in the body, something fitted and smooth. Depending on whether you are short waisted, regular, or long waisted will also come into play because you need to adjust the rise of whatever bottoms you are wearing in order to have space between your chest and pant’s waist. That one applies to all bust sizes though. Play around with the rise to see if that gives a different look.