CBK is the Cool Girl Blueprint — Here’s How to Get Her Look

Carolyn Bessette Kennedy, a true fashion icon of the 90s, has become a contemporary icon for style thanks to Ryan Murphy’s “Love Story.” Between her perfectly touched up bleach blonde roots, staple headbands and minimalist outfits, her cool, refined look is one that trend chasers have been seeking to emulate. Her outfits are best defined by a sleek, understated look that championed designers wear without showing off labels — a common aesthetic of the quiet luxury crowd.

More than just a Blair Waldorf or Charlotte York statement piece (IYKYK), headbands were central to a majority of CBK’s streetwear paparazzi shots. From simple, minimalist black headbands to glossy tortoise shell bands — these hair pieces were central to her outfits. These 90s and early 2000s hairpiece relics are an effective way to elevate an otherwise casual everyday look while keeping hair strays at bay.

Often spotted wearing a longline trench coat, Carolyn Bessette Kennedy frequently gravitated to it as a go-to. She typically opted for black (and the occasional tan) trench coats, which offer a sharper, more mysterious look that works perfectly over everything from athleisure to evening wear. The key to the CBK trench is the length. It should hit knee level down to mid-calf to create that iconic silhouette that makes any outfit look intentional and expensive.

CBK was the queen of straight-leg jeans. She famously avoided the ultra-baggy trends of the mid-90s, opting instead for classic blue or black denim with a mid-to-high rise. Her go-to was often a vintage Levi’s 517 or 501 cut. Ideally there should be zero distressing; the denim should look clean, paired with a tucked-in white button-down or a black turtleneck or simple blouse.

You can’t talk about Carolyn without mentioning the Little Black Dress. Whether it was a slinky silk slip or a structured off-the-shoulder midi, she understood that a black dress is a necessary staple in any iconic wardrobe. For your own wardrobe, look for either a mini or midi dress that skims the body in all the right places as a canvas for a date night look or a night on the town.

Footwear was where CBK pulled together all of her looks. For a night out, she leaned into the classic kitten-heel. For her daily commute through Manhattan, she was the blueprint for the polished black loafer. This basic but effective approach to footwear ensures you look put-together without feeling like you're trying too hard to be formal.

The Carolyn Bessette Kennedy lookbook has one golden rule: less is more. You’ll rarely see photos of her in chunky necklaces or statement earrings. Her jewelry was usually limited to a single pair of gold hoops or a classic analog watch. This minimalism in accessorizing is what allows the silhouette of the clothes to be a focal point. If you like a little extra, a single gold necklace or a silk scarf tied around your neck will add that zhuzh without being overly visually demanding.

Nothing says 90s chic like a pair of oval-shaped sunglasses. CBK was rarely seen outdoors without her signature monochromatic black tortoiseshell frames. These shades are complementary on most faces and help accomplish that off-duty model look. Avoid the oversized square glasses; the trend is all about the slim, elongated oval that fits tightly to the face.

Finally, the functional finishing touch: the oversized black tote. She was often photographed carrying a structured, logo-less black bag that held her entire life. It was less about wearing a statement bag and more about a high-quality leather piece which suits the overall look better.