16 Style Lessons to Learn from Jackie Kennedy

By Andrea Cheng
Updated May 29, 2016 @ 7:30 am
Credit: Getty Images

One doesn't become a style icon without a signature look. For Jackie Kennedy, that meant well-tailored skirt sets often paired with her perfectly coordinated pillbox hat and white gloves—a look (aka the "Jackie") that not only forever set the bar for First Lady fashion, but was also deeply adored, even decades after her time in office. 

But as much as we love her work uniform, it was her string of effortless off-duty ensembles that proved just how much innate chicness coursed through her. Take this candid photo of Jackie captured by paparazzo Ron Galello in 1971 (see, top), for instance. With the wind-whipped strands, the confidently simple henley tee and jeans, her trademark round shades in hand, it's a portrait that encapsulates undone perfection at its best—a look that so many can only hope to emulate.

All of this is to say, there's a lot to learn from this icon. So we dug through the archives and unearthed the most brilliant examples of Jackie Kennedy's style during every kind of occasion, from formal affairs to nautical excursions to street-chic errands. Scroll through and study up on these 16 style lessons to channel Jackie whenever you can. 

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Do the Crop

Credit: ANTONIO DI FILLIPO/REX/Shutterstock

Culottes are currently in, but the shin-grazing length was once popularized by this original street style star. Instead of neutrals or soft shades, Jackie struck bold with a siren-red pair that she color-blocked with a navy shirt (with sleeves haphazardly scrunched up) and styled with a studded wide belt and block-heel sandals.

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When in Doubt, Stick to the Basics

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Jackie's look is made up of wardrobe fundamentals, but there's nothing basic about it. She was the epitome of effortlessly chic in a ribbed henley shirt, no-frills denim, and round shades (clutched in her grip).

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Make Your Base Layer Stand Out

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How modern is this?! Jackie gave a couple of her classics—a navy trench and knee-high boots—a nice pop of color with her striped cherry-red turtleneck layered underneath.

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Color-Block with Separates

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A gown for a black-tie affair? Please. Jackie pieced together a stunning look, color-blocking with a black square-neck top, a sweeping marigold yellow ball skirt, and white bicep-high opera gloves.

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Experiment with Patterns

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Just when you thought you had the former First Lady's style figured out, she threw a fast one on us and surprised with a playful white-and-black zig-zag cocktail dress that she paired with a pair of black snub-nose ballet flats. Lesson to learn here: Let loose and have fun (YOLO and all that). 

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Balance Menswear with a Bow

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Jackie offset the masculinity of her suit separates with a substantial bow affixed at the collar of her shirt, which not only offered a nice boost in femininity, but also evoked an arty-cool intellectual vibe that's so very now (think: Gucci under Alessandro Michele's direction).

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Play with Opposites

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They may be coordinated separates, but Jackie must have known that a boxy cropped jacket would give her slim pencil skirt an extra dose of interest.

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Achieve an Air of Mystery

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A headscarf (bonus if it's Hermes) + square shades = the perfect look if you're planning to go incognito (or if you're suffering from a bad hair day). 

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Shrug On a Statement Coat

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Consider this the fail-safe way to make a statement during the colder months—a leopard-print coat that's both fiercely cool and classic. 

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Stand By Your Go-Tos

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Simple black layers got the patented Jackie Kennedy spin when she styled them with some of her signatures, like her square shades, her white gloves, and loafers.

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Dress Up a Basic Tee

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A basic white tee is a closet staple for a reason—it's so versatile that it can be dressed down or in Jackie's case, up, when styled with a leather mini, a croc chain-strap purse, a chic headscarf, and buckled flats.

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Bare Your Shoulders

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The off-the-shoulder silhouette is a trend that's going strong, but it was Jackie who showed us that this was the most demure, yet the most alluring way to expose skin. Her collarbone game = strong.

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Heighten Color Contrast

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Jackie dialed up the contrast when she styled her pale tailored separates with dark, saturated extras, including a belt that nipped in the waist, a darling mini purse, and a black pillbox hat.

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Skip Breton Stripes for Head-to-Toe White

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Chic ahoy! For a day out on the water, Jackie mastered monochromatism and lightened up in head-to-toe white, from her headscarf and shades right down to her sandals.

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Cinch with a Statement Belt

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Accentuate and draw attention to your waist simultaneously by throwing on an exquisitely ornate belt. Plus, it helps break up too much of one color. 

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Embrace the Decade of Your Time

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Jackie celebrated her 40th in 1969 in the most current way possible: with '70s fashion. She partied it up in a printed A-line dress that she accessorized with a strand of double-wrapped pearls and disco drop earrings.

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By Andrea Cheng