Carolyn Bessette-Kennedy Is My Leopard-Print Muse—4 Ways to Wear It Like Her

If you're simultaneously obsessed with the latest micro-trends and too intimidated to test them out, you've come to the right place. This is Ways to Wear, a monthly series where editor Eliza Huber offers a dose of outfit inspiration focused on current trends that feel intriguing yet overwhelming at the same time. Consider it your guide to actually wearing the coolest items of the moment, no matter how puzzling they might appear at first.

In fashion, a few years never pass by without at least one person trying to make leopard print a thing again. The kitschy print will show up in a runway collection or outside of one of L.A.'s many celebrity hot spots (yes, I'm looking at you, Sushi Park and Giorgio Baldi) in the form of a velvet coat or pair of loafers, leading to a bevy of content surrounding its return to fashion's good graces. It rarely sticks, though, and I think I know why. 

Whenever leopard print has become a "trend," it's always done so in a way that feels excessive or over-the-top, but the times when it's felt the most covetable are when it's worn in a casual, laissez-faire manner that allows whatever item it's printed on to become a timeless staple. There's a reason why my leopard-print mood board doesn't include very many images from the handful of times that leopard print has made waves in the last two decades. Instead, it mostly consists of photos from the '80s and '90s, where it's donned by off-duty models and New York City muses completely nonchalantly—with jeans and a tee or a black turtleneck and matching pencil skirt. To make leopard print work, it has to appear effortless. No one managed to do just that better than Carolyn Bessette-Kennedy.

Known for her innate ability to look elegant no matter what she was wearing—be it dark jeans and flip-flops for a dog walk around Tribeca or a gown for one of the many black-tie galas she attended alongside her husband John F. Kennedy Jr.—the late publicist and socialite is the perfect muse for anyone trying to work leopard print into their wardrobe without doing too much. 

Her wardrobe only included a few leopard-print pieces (a knee-length, collared coat discovered at a flea market, according to British Vogue, and a pair of heeled loafers), but Bessette-Kennedy wore them frequently enough for the print to become synonymous with her iconic minimalist wardrobe, which heavily featured Prada and Calvin Klein, where she worked in PR. Typically, their appearances were accompanied by lots of black. Think turtlenecks, T-shirts, coats, and sweaters paired with just-flared-enough dark-wash denim. She never wore two leopard-print pieces together in one outfit and always kept the accompanying colors simple and classic. 

When I decided to try my hand at incorporating the print into my own wardrobe, I likewise kept each look to just one printed piece and stuck to mostly black accent items. Keep scrolling to check out the four ways I ended up styling leopard print with Bessette-Kennedy at the forefront of my mind. 

What You'll Need: Black Blazer + Black Pencil Skirt + Leopard-Print Handbag

Ever since I saw Ferragamo's leopard-print offering, which began with a runway look from the fall/winter 2023 show, I've felt inspired to find that perfect printed piece to add to my wardrobe. In the show, the model wore a leopard-print belted coat with matching wedge heels and a purse to go with. It's bold—bolder than I would probably feel comfortable doing on any regular day at the office or on any occasion really—but that didn't stop it from convincing me that right now is the perfect time to dip into the leopard-print pool. 

That said, when I decided to do this story, Ferragamo was my first stop. This rectangular, briefcase-like bag is what spurred me to create a corporatecore ensemble, pairing with it a cropped high-neck blazer, a midi-length pencil skirt, and extra-sharp Prada wedges. Naturally, I had to add a pair of fishnet tights to break up all of the solid black and balance out the whole look. The result? My realization that even something as small as an eight-inch-long handbag can turn anything into an outfit when it's made of elegant pony hair and painted with a bold cheetah pattern. 

Wearing: Zara blazer and skirt; Ferragamo Wanda East-West Top Handle ($3000); Calzedonia tights; Prada shoes; Linda Farrow sunglasses; vintage earrings

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What You'll Need: Leopard-Print Blazer + Black Fitted Trousers + Kitten Heels

On my search for leopard-print outerwear, I stumbled upon this velvet oversize blazer at Raey, Matches's fashion-favorite in-house label, which was paired with matching trousers on the site. A top-to-toe look wouldn't have been very CBK, but as a separate, the blazer itself was too tempting to not at least try to transform into a casual piece with the right styling. My solution was to use the belt it came with to tighten up the blazer as much as possible and make it feel a bit more tailored. Then, I swapped out the leopard pants for some super-fitted vintage Gucci trousers from my closet and kitten-heel Prada pumps. The goal was to take the loud centerpiece and hush it up a bit with pieces from the best era for minimalism and items inspired by that time.

Wearing: Raey Exaggerated Leopard Cotton-Velvet Tux Blazer ($965); Gucci pants; Prada shoes; Linda Farrow sunglasses

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What You'll Need: Leopard-Print Dress + Black Elbow-Length Gloves + Black Boots

One of my all-time favorite Carolyn Bessette-Kennedy looks is one she wore to the the Municipal Art Society gala in 1998. For the occasion, she wore a strapless black gown from Japanese designer Yohji Yamamoto's F/W 98 collection alongside a pair of matching velvet opera gloves, according to i-D. The look has stuck with me for years, so when I found this leopard-print dress by Raey, I knew it had to be accompanied by a pair of opera gloves. Luckily, my co-worker Jasmine recently secured a pair of Jil Sander leather gloves when she was traveling in Italy and kindly let me borrow them to complete my look. From there, I added point-toe stiletto Jimmy Choo boots that are fitted through the leg, keeping the outfit feeling formal but not inappropriate for the season aka the dead of winter. 

Wearing: Raey Leopard-Print Bandeau-Neck Crepe Midi Dress ($372); Jil Sander gloves; Jimmy Choo boots; Bottega Veneta Drop Earrings ($820); Linda Farrow sunglasses

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What You'll Need: Leopard-Print Jacket + Oversize Trousers + Black Handbag 

I've actually had my eye on this Tory Burch hourglass-fitting jacket for a few years now—yes, years—and for some reason, I kept telling myself that the print was too out-there for a minimal dresser like myself. This story gave me an excuse to finally take it for a test-drive and determine if the devil on my shoulder that had been whispering away for all this time was either right or completely misinformed. Hint: It's the latter. The shape of the jacket, for starters, is impeccable, which is why I wanted to keep the rest of the outfit super pared back, allowing it to be the centerpiece through and through. To do so, I chose some oversize Staud trousers, black Mary Jane flats, and my black 1995 Re-Edition Prada bag that Bessette-Kennedy was famous for carrying regularly back when the original style came out in the '90s. (In fact, it's unofficially referred to as the Carolyn bag, according to Vogue.) 

Wearing: Tory Burch Reversible Printed Jacket ($399); Staud Luisa Pleated Wide-Leg Pants ($345); Prada Re-Edition 1995 Carolyn Nappa Leather Bag ($3500); Massimo Dutti shoes; Rolex watch; Linda Farrow sunglasses

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