Fashion style

Cold weather outfits inspired by the classic Carolyn Bessette-Kennedy look

As the trends of the 2000s and 90s take the fashion world by storm (and show no signs of letting up), sometimes it can be easy to feel left behind by fashion trends. used to be, especially if butterfly hair clips and low-rise jeans aren’t for you.

However, the beauty of the 90s through the 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 – come in, Carolyn Bessette -Kennedy.

Carolyn Bessette-Kennedy, a publicist for Calvin Klein, came to public attention when she dated and married John F. Kennedy Jr. (son of President John Kennedy and Jackie Kennedy Onassis). The couple were hounded by the paparazzi and later 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 all the rage. She preferred simple looks (and, of course, often bought her own closet and was an outfit repeater!), liked a good pair of jeans, heeled boots and simple mid-length coats, and tended towards black and camel or neutrals like denim.

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

Mid-length camel 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, swap out simple gold studs for a pair of statement earrings.

Bootcut 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 like a black turtleneck, white t-shirt, or white oxford shirt . She has been photographed wearing this look again and again and again.

Easily swap with a classic white tee or add a touch of vintage glamor 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 also reminds why mixing black and shades of brown is acceptable and chic!

Black dress + black coat + slingback heels + lipstick


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

Beyond sunglasses and a handbag 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 long skirt + silk buttons + strappy heels + fashion bag


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

Once again, Carolyn Bessette-Kennedy shows us that elegance is understated, leaving all the talk to her glamorous mini handbag with golden links.

Hazel J. Edmonds

The author Hazel J. Edmonds