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Carolyn Bessette Kennedy's chic sense of style earned her fashion icon status in the 1990s. Now, women everywhere are revisiting her timeless aesthetic as a new FX series titled Love Story revisits Bessette Kennedy's highly publicized relationship with John F. Kennedy Jr.
The fashionista was known for her ageless, classic ensembles that still stand the test of time today, so Parade consulted celebrity stylist Julie Matosto discover seven ways to recreate Bessette Kennedy's style for women over 50.
Throughout her relationship with JFK Jr., Bessette Kennedy exuded a sense of sophistication and class with both her red carpet and street style looks. From glamorous eveningwear to sleek everyday ensembles, she nailed the art of looking effortlessly put together. She also had an enviable accessory game, and was known for rocking her signature headbands.
One of the most relatable aspects of Bessette Kennedy's fashion sense was its timeless nature. Matos, who has worked with Cobie Smulders, Natalie Dormer, Julianne Moore and other celebrities, specializes in creating fashion-forward looks for women over 50. Below, she shares five of Bessette Kennedy's most iconic looks, specific recommendations for channeling her signature style in your own life and more.
Related: 8 Fashion Mistakes That Instantly Age You—and What To Do Instead, Celebrity Stylists Say
Bessette Kennedy was best known as the wife of JFK Jr., but there was so much more to her story.
Born in 1966, Bessette Kennedy had twin older sisters, Lisa and Lauren Bessette. Bessette Kennedy had a successful career working as a publicist and VIP associate for fashion designer Calvin Klein.
After Bessette Kennedy and JFK Jr. met in the early '90s, they tied the knot in an intimate wedding ceremony in 1996.
In 1999, Bessette Kennedy died in a plane crash that also killed her husband and sister, Lauren Bessette.
Related: 7 Best Dresses for Women Over 50, According to a Celebrity Stylist
What Was Carolyn Bessette Kennedy's Iconic Style?
Matos says Bessette Kennedy epitomized "modern minimalism" before the term even held true meaning.
"She relied on clean silhouettes, neutral palettes and incredibly well-cut basics. Nothing looked over-styled. It was always effortless but intentional," the stylist tells Parade.
Restraint was at the core of Bessette Kennedy's iconic style.
"She understood that a perfectly cut coat, a simple slip dress or straight-leg denim could be more powerful than anything trend-driven. Her wardrobe was built on timeless pieces that worked season after season," Matos says.
The stylist notes that this philosophy is particularly relevant for women over 50.
"The focus shifts from chasing trends to investing in beautiful fabrics, great tailoring and pieces that feel confident and polished," she explains.
Related: 7 Best ’50s Fashion Looks, According to Celebrity Stylists
How To Dress Like Carolyn Bessette Kennedy at Any Age
1. Effortless tailoring
Rose Hartman/Getty Images
Why it's iconic: "Carolyn understood that great style starts with impeccable tailoring. When something fits perfectly and the silhouette is clean, the entire look feels elevated without needing excess styling," Matos says.
Why it works at any age: Tailored looks, especially tailored outerwear, are "universally flattering and instantly sophisticated," per Matos.
Shop the look:
Ann Taylor Colorblock Crew Neck Shift Dress ($169)Tommy Hilfiger Keyhole-Neck Sheath Dress ($139)Related: The 7 Most Comfortable Pants To Wear To Work in 2026, According to a Celebrity Stylist
2. Elevated everyday style
Evan Agostini/Liaison/Getty Images
Why it's iconic: "One of Carolyn’s greatest style strengths was her ability to make everyday pieces look incredibly chic. Jeans, a great coat and simple accessories became her signature uniform," Matos says.
Why it works at any age: The stylist notes that high-quality basics make a wardrobe timeless at any age. "Crisp shirts, denim and classic coats form the foundation of effortless style for women of every generation," she says.
Shop the look:
Draper James Woods Coat in Red ($199, originally $298)Marshalls Democracy Ab Tech High Rise Out There Flare Leg Jeans ($39.99)3. Beauty in black
Richard Corkery/NY Daily News Archive via Getty Images
Why it's iconic: "What made Carolyn’s style so iconic was her restraint. She relied on neutral palettes, clean silhouettes and classic pieces—an approach that always feels modern no matter the decade," Matos says.Why it works at any age: "Neutral tones and streamlined silhouettes create a refined look that transcends trends. This minimalist formula allows women to look polished without feeling over-styled," the stylist explains.
Shop the look:
White House Black Market Off-The-Shoulder Crepe Jumpsuit ($138.75, originally $185)HSN G by Giuliana Sleeveless Crossover Jumpsuit ($34.95, originally $69.95)4. Understated evening glamour
Donato Sardella/Penske Media via Getty Images
Why it's iconic: "Carolyn’s evening style proved that simplicity can be incredibly powerful. A sleek silhouette and luxurious fabric often make a far stronger statement than embellishment," Matos says.Why it works at any age: Minimalistic eveningwear lends a timeless vibe to your style since it focuses on "fit and elegance rather than trends," per Matos.
"Clean lines and beautiful fabrics create a look that remains sophisticated for decades," she says.
Shop the look:
Good American Luxe Suiting Exec Blazer Dress ($199)Anne Klein Asymmetric-Neck 3/4-Sleeve Midi Dress ($129)5. Effortless event dressing
Justin Ide/Getty Images
Why it's iconic: "What made Carolyn’s style so enduring is how effortless it always felt. She relied on beautifully cut pieces and a restrained palette, proving that true sophistication comes from simplicity rather than excess," Matos says.
Why it works at any age: Matos says this particular look, which Bessette Kennedy wore to an event in 1999, reflects her signature formula of "clean lines, elegant tailoring and minimal accessories."
"Those elements create a timeless silhouette that works for women of any age because the focus is on fit, proportion and understated elegance rather than trends," she explains.
Shop the look:
Donna Karan New York One-Button Peplum Jacket ($209) and High-Waist Mid Rise Pants ($139)Inspire Chic Business Peplum Blazer and Pencil Skirt Suit Set 2 Pcs Small Black ($64.99, originally $86.99)Related: 9 Best Work Dresses for the Office, According to a Celebrity Stylist
7 Ways To Recreate Carolyn Bessette Kennedy's Style for Women Over 50, According to a Stylist
1. The neutral palette
Gotham/GC Images/Getty Images
"Hailey Bieber frequently embraces monochrome neutral looks that mirror Carolyn’s signature palette," Matos tells Parade.
How women over 50 can recreate the look: The stylist recommends sticking to shades like black, cream, camel and navy.
"When the palette is simple, the quality and tailoring of the clothing really stand out," she says.
Shop the look:
Mersea Chelsea Kimono ($198)Karl Lagerfeld Paris Color Block Trench Coat ($249)2. The slip dress
Taylor Hill/WireImage
"A simple slip dress captures the understated elegance Carolyn wore so well. [This] version shows how powerful a clean silhouette can be without heavy embellishment," Matos says.
How women over 50 can recreate the look: The stylist notes that layering is the key for women over 50.
"Add a blazer, long coat or refined knit over the slip dress. It keeps the look sophisticated while still feeling modern and effortless," she says.
Shop the look:
Loft Versa Satin Maxi Slip Dress ($49, originally $99.95)Express Satin Cowl Neck Sleeveless Slit Maxi Slip Dress ($79, originally $98)3. The white shirt
Marc Piasecki/GC Images
Victoria Beckham has built much of her personal style around pieces Carolyn would have worn: crisp shirting, tailored trousers and minimal accessories, Matos says.
How women over 50 can recreate the look: The stylist calls a white button-down shirt a "wardrobe cornerstone for women over 50" since it’s "endlessly versatile."
"Wear it with tailored pants, a midi skirt or even great denim. The key is keeping the styling relaxed but polished," she tells Parade.
Shop the look:
Marshalls Kobi Halperin Gina Blouse ($99.99)Ann Taylor Oversized Pocket Shirt ($62.65, originally $89.50)Related: The 9 Most Stylish Ways To Wear UGGs, According to Celebrity Stylists
4. Straight-leg denim
RB/Bauer-Griffin/GC Images
"Jennifer Aniston’s off-duty style often reflects the same quiet luxury Carolyn embodied. Straight-leg denim paired with simple basics creates a look that feels polished but easy," Matos says.
How women over 50 can recreate the look: The stylist says straight-leg denim is "far more flattering than overly distressed or trend-driven styles" for women over 50.
"It elongates the leg and works beautifully with blazers, sweaters and classic coats," she says.
Shop the look:
Loft Rivete Mid Rise Slim Jeans in Vintage Mid Wash ($66.46, originally $94.95)HSN DG2 by Diane Gilman Lux Touch Denim Straight-Leg Jean ($59.95, originally $65.95)Related: 7 Best Jeans Styles for Women Over 50, According to Celebrity Stylists
5. The slip skirt
Jose Perez/Bauer-Griffin/GC Images
"Katie Holmes frequently leans into minimalist silhouettes that echo Carolyn’s aesthetic. A slip skirt paired with a simple knit or shirt feels elegant without trying too hard," Matos says.
How women over 50 can recreate the look: The stylist calls a slip skirt a "fantastic alternative to trousers" for women over 50.
"It moves beautifully and can be styled with boots, flats or heels depending on the occasion," she reveals.
Shop the look:
QVC Susan Graver Regular Satin Pull-On Midi Skirt ($57.98, originally $64)Topshop Satin Maxi Skirt ($42, originally $60)6. Strategic accessories
Moritz Scholz/Getty Images
According to Matos, this look perfectly captures the kind of restraint Carolyn Bessette Kennedy was known for. The outfit is clean and tailored, and the accessories are subtle but intentional. Nothing is competing for attention. Everything feels balanced.
How women over 50 can recreate the look: The stylist says accessories should "finish the look, not overwhelm it."
"Think small gold hoops, a classic watch, refined sunglasses or a simple leather bag. When the pieces are minimal and chosen well, the entire outfit feels more elevated and sophisticated," she says.
Shop the look:
Karl Lagerfeld Paris Evelina Bucket Bag ($348)Kaliyadi Round Polarized Sunglasses ($13.43, originally $21.99)Related: How To Layer Necklaces: 6 Best Ways, According to Celebrity Stylists
7. The camel coat
Alessio Botticelli/GC Images
"Rosie Huntington-Whiteley often channels the same clean minimalism Carolyn was known for. This camel coat look works because the silhouette is structured but not stiff, and the palette stays neutral," Matos tells Parade.
How women over 50 can recreate the look: The stylist calls a camel coat "one of the smartest investments" for women over 50.
"It instantly elevates denim, tailoring or even a knit dress. Look for strong tailoring and beautiful wool. That’s where the polish comes from," she says.
Shop the look:
Madewell Double-Faced Brushed Long Coat ($149.99, originally $368)Quince Italian Wool Classic Single-Breasted Coat ($175, originally $698)Up Next:
Related: How Carolyn Bessette-Kennedy’s Iconic Style Helped Shape Sarah Pidgeon’s 'Love Story' Role
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Julie Matos, stylist who's worked with Cobie Smulders, Natalie Dormer, Julianne Moore and other celebritiesHence then, the article about 7 ways to recreate carolyn bessette kennedy s style for women over 50 according to a stylist was published today ( ) and is available on Parade ( Saudi Arabia ) The editorial team at PressBee has edited and verified it, and it may have been modified, fully republished, or quoted. You can read and follow the updates of this news or article from its original source.
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