How to shop Carolyn Bessette's iconic '90s looks

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Carolyn Bessette-Kennedy, an American publicist who married John F. Kennedy Jr., has re-emerged as the ultimate style icon.

Her influence is a testament to the enduring appeal of her effortlessly chic aesthetic, characterised by timeless basics and a distinctly '90s minimalist vibe.

Carolyn Bessette-Kennedy was the definition of quiet luxury, as she opted for a pared-back wardrobe of carefully chosen pieces, focusing on tailoring, quality fabrics, and a neutral colour palette of black, white, grey, camel, and navy.

Shop her looks below.

Let's kick things off with a classic Carolyn Bessette-Kennedy look: her iconic approach to formal wear. While most of us aren't heading to a black-tie event on the regular, the beauty of this style lies in its adaptability. She famously paired elegant skirts with a crisp white button-up shirt, instantly making the outfit more approachable.

If you wanted to dress this look down for everyday wear, swap a maxi skirt for a mid-length skirt for versatility. Embrace a slightly oversized button-up for a relaxed silhouette, and trade high heels for kitten-heel strappy sandals.

Shop her look with this COS Relaxed Cotton Shirt for $139, & Other Stories Asymmetric Ruffle Midi Skirt for $101.25, and a pair of Caprice Black Kid Heels from Tony Bianco for $169.95.

If there's one thing Carolyn Bessette-Kennedy truly mastered, it was the art of elevating an everyday outfit. Her signature pairing of blue jeans with a black sleeveless turtleneck, complemented by simple accessories and strappy block heels, is a perfect example of this.

It's a look that remains utterly timeless and elegant, proving that some styles simply don't need updating to stay relevant.

To shop her look, try Tussah Meadow Knit Top for $24.50, 501 Original Jeans from Levi's from $55.98, a CENDRE Kelly Watch for $239, and a pair of Ravella Geisha Smooth Sandals for $62.97.

Another signature Carolyn Bessette-Kennedy look is her perfect take on the black midi dress paired with pointed black heels. This outfit is all about the dress's shape, tailoring, and style – it truly speaks for itself. It's the kind of outfit that doesn't need much else to shine.

To make this look more timely for today, simply opt for a black midi dress that cuts off at the mid-calf, offering a modern silhouette. Then, swap out the traditional black pumps for a slingback pointed toe pump.

To shop this look, get the MESHKI Amelita Suiting Halter Midi Dress in Black for $189, and the Billini Kyrie heels for $89.95

This is arguably my absolute favourite Carolyn Bessette-Kennedy outfit, perfectly capturing that iconic '90s fashion.

Honestly, I'd wear this exact look today because it's just that timeless. But if you want to make it a little more contemporary, consider swapping the pencil skirt for a slip-style midi skirt, and go for a thinner heel on the boots.

Shop her look with the Uniqlo 3D Knit Seamless Cotton Relaxed V Neck Jumper in Black for $39.90, Stella Isla Skirt in Beige for $132.30, Tony Bianco Fantasy Boots in Cognac Vintage for $299.96, and the Ariel Shoulder Bag from Nine West for $50.97.

Last but certainly not least, we have this absolutely gorgeous winter outfit that just exudes effortless chic. It's as timely now as it was then, and this is my official request to bring back headbands as a staple accessory.

To shop this look, get the Uniqlo 100% Merino Ribbed Turtleneck Sweater for $39.90, Wrangler Claudia Hi Straight Jeans for $127, Sadie Coat from Assembly Label for $280, Alias Mae Ivana Loafers for $249.95, Le Specs Outta Love sunglasses for $52.50, and a Morgan & Taylor Katelyn Faux Leather Headband for $29.95.

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