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As Y2K and 90s trends take the fashion world by storm (and show no sign of letting up), it can sometimes be easy to feel left in the dust with the fashion trends of yore, especially if the butterfly hairclips and lowrise jeans are not for you.

However, the beauty of the 90s through Y2K style eras is that there is something for everyone: bubblegum pop fun (Britney Spears and the Spice Girls), grunge (think Winona Ryder and Drew Barrymore) or a more classic look – enter, Carolyn Bessette-Kennedy.

Carolyn Bessette-Kennedy, a publicist for Calvin Klein, came to the public’s attention when she dated and married John F. Kennedy Jr. (son of President John Kennedy and Jackie Kennedy Onassis). The couple was hounded by the paparazzi and subsequently admired for their street style. However, they tragically died in a plane crash in 1999.

Bessette-Kennedy’s timeless look was a favorite long before 90s nostalgia became vogue. She favored simple looks (and, evidently, often shopped her own closet and was an outfit repeater!), loved a good pair of jeans, heeled boots, and simple mid-length coats, and tended toward black and camel or neutrals like denim.

Bessette-Kennedy’s outfits are the perfect inspiration for someone aspiring to find a simpler outfit formula or who would like to cultivate a capsule wardrobe. Here are five outfits inspired by Bessette Kennedy’s most classic looks.

Camel Midi Skirt + Black Sweater + Brown Heeled Boots


01. Banana Republic Factory, $30 / 02. Lulu’s, $140 / 03. Gorjana, $32 / 04. Mango, $50 / 05. Banana Republic Factory, $54.00

Like many of Bessette-Kennedy’s looks, the outfit could be perfect for work and chic at a holiday gathering. If maximalism is more your style, substitute the simple gold studs for a pair of statement earrings.

Boot Cut Jeans + Boots + Classic Top


01. Gap, $70 / 02. Urban Outfitters, $17 / 03. Zara, $70 / 04. Amazon, $13 / 05. Madewell, $138 / 06. Nordstrom Rack, $80

This is the outfit most associated with Carolyn Bessette-Kennedy: bootcut jeans, heeled boots (or heeled loafers), and a simple classic top such as a black turtleneck, white t-shirt, or white oxford button-down. She was photographed wearing this look over and over and over again.

Easily swap in a classic white t-shirt or add a touch of vintage glamour with a leopard print coat.

Utility Pants + Ribbed Turtleneck + Loafers + Oval Sunglasses


01. Old Navy, $23 / 02. Good American, $95 / 03. Urban Outfitters, $17 / 04. Mango, $100 / 05. Sam Edelman, $150

Like the majority of Carolyn Bessette-Kennedy’s outfits, this one can be easily replicated over 20 years later. Bessette-Kennedy is also a reminder of why mixing black and shades of brown are acceptable and chic!

Black Dress + Black Coat + Slingback Heels + Lipstick


01. Zara, $70 / 02. Marine Layers, $118 / 03. ASOS, $40 / 04. Clinique, $22

Beyond sunglasses and a purse or clutch, Bessette-Kennedy rarely accessorized with jewelry, and even at elegant events, she kept her hairstyle simple. In this outfit, she accessorized with lipstick, showing us that sometimes less is more. 

Black Maxi Skirt + Silk Button Down + Strappy Heels + Statement Bag


01. Zara, $50 / 02. Quince, $60 / 03. Princess Polly, $40 / 04. Vince Camuto, $85

Again, Carolyn Bessette-Kennedy shows us that elegance is understated, leaving all the talking to her glamorous, gold-chainlink mini purse.