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.
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.
Related: 8 Fashion Mistakes That Instantly Age You—and What To Do Instead, Celebrity Stylists Say
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.
In 1999, Bessette Kennedy died in a plane crash that also killed her husband and sister, Lauren Bessette.
What Was Carolyn Bessette Kennedy's Iconic Style?
Matos says Bessette Kennedy epitomized "modern minimalism" before the term even held true meaning.
Restraint was at the core of Bessette Kennedy's iconic style.
The stylist notes that this philosophy is particularly relevant for women over 50.
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 works at any age: Tailored looks, especially tailored outerwear, are "universally flattering and instantly sophisticated," per Matos.
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 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
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
"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 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."
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
How women over 50 can recreate the look: The stylist recommends sticking to shades like black, cream, camel and navy.
Shop the look:
Mersea Chelsea Kimono ($198)Karl Lagerfeld Paris Color Block Trench Coat ($249)2. The slip dress
Taylor Hill/WireImage
How women over 50 can recreate the look: The stylist notes that layering is the key for women over 50.
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
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."
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
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.
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
How women over 50 can recreate the look: The stylist calls a slip skirt a "fantastic alternative to trousers" for women over 50.
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
How women over 50 can recreate the look: The stylist says accessories should "finish the look, not overwhelm it."
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
How women over 50 can recreate the look: The stylist calls a camel coat "one of the smartest investments" for women over 50.
Shop the look:
Madewell Double-Faced Brushed Long Coat ($149.99, originally $368)Quince Italian Wool Classic Single-Breasted Coat ($175, originally $698)Related: How Carolyn Bessette-Kennedy’s Iconic Style Helped Shape Sarah Pidgeon’s 'Love Story' Role
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