2 min readIf you’re anything like me, you’ve probably been glued to the weekly episodes of Love Story: John F. Kennedy Jr. & Carolyn Bessette (Episode 5 just dropped, in case you missed it). Yes, the romance is swoon-worthy—but alongside the love story, something else is stealing the spotlight: Bessette Kennedy’s effortlessly chic style, which has fashion obsessives everywhere taking notes.
Timelessly sophisticated, refined, and elegant, Bessette Kennedy favored versatile staples, quality basics, and impeccably tailored silhouettes. And with fashion’s recent shift away from overt branding and toward understated, enduring style, it’s no surprise we’re once again looking to emulate her iconic aesthetic. We’ve already broken down how to channel her ’90s wardrobe, but there’s another category just as deserving of attention: her accessories. Whether it was a tortoiseshell headband, sleek rectangular sunglasses, polished loafers, a structured handbag, or minimalist gold jewelry, her accessories always felt intentional—elevating her look without ever overwhelming it.
So if you’re a fan of Bessete Kennedy’s style, consider this your sign to invest in classic, versatile, and impossibly chic accessories. Ahead, discover the pieces that’ll elevate any outfit in an instant.
The Black Leather Handbag
Timeless, structured black handbags never fall out of favor. Carolyn Bessette Kennedy famously carried a classic black Hermès Birkin 40 and was often photographed with Prada’s 1995 Spazzolato bag tucked under her arm. Today, you can still shop the re-edition, along with a range of similarly sleek styles.
Verafied Allure Shoulder Bag
Kattee Soft Genuine Leather Shoulder Bag
Lié Studio The Lou Patent Leather Bag
Prada Large Re-Edition 1995 Leather Handbag
DeMellier London The Hudson
The Classic Loafer
A true shoe-rack staple, leather loafers pair effortlessly with denim, tailored trousers, midi dresses, and more—and Bessette Kennedy was often spotted in the comfortable classic. Wear them solo or with socks to instantly elevate an off-duty uniform with understated polish.
Black Suede Studio Arrow Loafer
The Tortoiseshell Headband
Bessette Kennedy often wore a headband—most frequently a simple tortoiseshell style. Beyond keeping flyaways at bay, it lent an understated polish, creating a sleek, slicked-back look that stayed perfectly in place.
France Luxe Skinny Headband
Camila Paris Durable Headband
Lele Sadoughi Tortoise Emma Acetate Headband
Oval Sunglasses
Now, this accessory offers an effortless way to channel Carolyn Bessette Kennedy’s elegant aesthetic. Oval sunglasses were a constant in her daily rotation, specifically slim frames with dark lenses that accentuated—rather than obscured—her features.
Aire Objective Sunglasses
Tom Ford Chloe 52mm Oval Sunglasses
Ray-Ban RB4472 Khal Bio-Based
Otra X Grandquist Kenny Sunglasses
Minimalist Jewelry
Bessette Kennedy favored dainty, timeless jewelry, often limiting herself to a single piece for an understated, minimalist effect. At times, it was a simple strand of pearls; at others, delicate pearl studs or a single cuff. To emulate her approach, opt for one refined piece at a time and let its simplicity make the statement.
Hainbag 6mm Freshwater Pearl Stud Earrings
Adina Reyter Tiny Seed Pearl Necklace
Frank Darling Lab Grown Diamond Tennis Bracelet
Oak and Luna Juno Diamond Necklace
Blue Nile Freshwater Cultured Pearl Stud Earrings
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