It’s 9 a.m. on a freezing January morning in Boston. Before class, I quickly style my hair with my tortoise hairbrush, put on a matching tortoise headband and grab my tortoise sunglasses before throwing on an oversized wool coat.
These pieces, now flooding my closet with that signature marbled pattern, have accumulated almost subconsciously after pinning countless photos of Carolyn Bessette-Kennedy’s outfits to my Pinterest boards. It wasn’t until a few days ago that I discovered she was a Boston University alum. Decades after she walked down Commonwealth Avenue, I had been following in her stylish footsteps — quite literally.
Now that “brat summer” has had its time, I declare Carolyn Bessette-Kennedy season officially open.
Her style — effortless and undeniably chic — is a timeless blueprint for the colder weather, with a sort of elegance that speaks quietly but powerfully. In fact, Bessette-Kennedy never gave an interview — she always let her clothes do the talking.
Her wardrobe centered around a few key pieces and styles, many of which have become essential in my own collection.
Bessette-Kennedy’s first staple: Tortoiseshell everything
From sunglasses to hair clips and headbands, I’ve found myself drawn to this warm, marbled pattern. It’s subtle, but makes a statement. Her signature tortoiseshell frames added an air of mystery to her outfits, and now, I can’t leave the house without mine—regardless of whether the sun is out or not.
The perfect outer layer: Oversized wool coats
These were another key item of Bessette-Kennedy’s winter uniform. She always made her outerwear the star of the show, and I’m all in. When it comes to coats, I say the bigger, the better. Whether in a neutral shade or a fun hint of leopard print, these coats are the perfect balance of cozy and chic. She’d pair it with a delicate necklace or a sleek handbag — accessories that felt like the perfect finishing touches. They never felt overdone, it was always just right.
Sometimes less is more: opting for simpler pieces
Regarding the core of her outfits, Bessette-Kennedy gravitated toward classic, understated pieces. Black, white, beige and navy made her outfits timeless and versatile. I’ve adopted this palette myself, and this has made it so easy to mix and match pieces without feeling repetitive. She kept jewelry to a minimum, but when she did wear something, it was always a classic pearl necklace. She was a woman of taste, I may say, as I also never leave my dorm without my cherished pearls.
Classic blue jeans were her go-to for casual days, and she nailed the laid-back, yet polished vibe every time. It is said that she spent countless hours thrifting for the best pair of jeans. She always had a New England charm to her looks, seemingly reminiscing on her Boston days. I can easily picture her heading to class down Commonwealth Avenue, her vintage jeans paired with leather boots, looking effortlessly chic as she picks up coffee on the way.
Carrying on Caroline Bessette-Kennedy’s legacy
What I love most about Bessette-Kennedy’s style is how effortlessly classy it was. She proved simplicity doesn’t have to be boring. Every piece in her wardrobe served a purpose, and the way she put them together felt intentional yet approachable.
But there’s a catch: everyone can dress like Carolyn Bessette-Kennedy, but not everyone can be Carolyn Bessette-Kennedy. Her “it girl energy” went far beyond the clothes. It was in the way she carried herself, with quiet confidence and a graceful presence.
By embracing her minimalistic staples, we not only honor her impeccable taste but also carry forward the legacy of a woman who proved that style is just as much about how you carry yourself as it is about what you wear. Carolyn Bessette-Kennedy’s influence lives on, and this winter, I’m more than happy to carry her legacy forward right where she shaped her iconic style!
