Honestly, if you close your eyes and think about a Jacqueline Kennedy Onassis dress, you probably see the pink one. You know the one. The strawberry-pink wool suit, the matching pillbox hat, and the horrifying dark stains from that November day in Dallas.
But there is so much more to her wardrobe than just that single, tragic moment. Jackie wasn’t just a "fashionista"—a word she probably would have hated. She was a master of political theater who used seams and buttons to send messages. She was also a bit of a rebel. Did you know she actually got in trouble for liking French clothes too much? It's true.
The Controversy Behind the "Chanel" Suit
Here is a weird fact: that pink suit wasn't actually made by Chanel in Paris. Sorta.
During the 1960 campaign, the press hammered Jackie for being "too French" and spending $30,000 a year on European couture. It made her look out of touch. To fix this, her husband—and the political machine—basically forced her to "buy American."
Enter Chez Ninon. This was a high-end shop in New York that basically functioned as a legal "knock-off" house. They would buy the patterns and the exact fabric from Chanel in France, then sew the garment in Manhattan so it could be labeled "Made in America." So, that iconic pink suit was a Chanel design, but it was assembled on Park Avenue.
When the assassination happened, Jackie famously refused to take the dress off. "Let them see what they've done," she said. She wore it during the swearing-in of LBJ on Air Force One, still covered in blood.
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Today, that dress is a ghost. It’s stored in a climate-controlled, windowless vault in the National Archives in Maryland. It has never been cleaned. And thanks to a deed signed by Caroline Kennedy, it won't be seen by the public until at least 2103.
The Secretary of Style: Oleg Cassini
While she loved her "line-for-line" French copies, Jackie needed a signature look that was uniquely hers. She hired Oleg Cassini. She even called him her "Secretary of Style."
They created a uniform.
- The A-Line silhouette: It hid her straight waist and highlighted her long legs.
- The Boatneck: This widened her shoulders.
- The Three-Quarter Sleeve: Perfectly designed to show off her gloves and wrists.
Cassini was a genius at color. When they went to India in 1962, he made her an apricot silk dress. Why? Because he knew it would pop against the crowds. It made her instantly recognizable from a mile away. It wasn't just a Jacqueline Kennedy Onassis dress; it was a beacon.
Why the Wedding Dress Was a Disaster (To Her)
Most people look at her 1953 wedding gown—the one with the massive skirt and the tiny wax flowers—and think it’s the height of bridal perfection.
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Jackie hated it. She wanted something sleek, simple, and "French." Instead, her mother and Joe Kennedy insisted on a "fairy tale" gown that looked like a lampshade. It was designed by Ann Lowe, a brilliant Black couturier who was largely ignored by the press at the time.
A week before the wedding, a pipe burst in Lowe’s studio and ruined the original dress. Lowe and her team worked around the clock to recreate it in days. Even though it's one of the most famous dresses in history, Jackie reportedly told friends she thought it made her look like a "bewigged Marie Antoinette."
From First Lady to Jackie O: The Big Shift
After JFK died and she eventually married Aristotle Onassis, the "Jackie Look" died too. The pillbox hats were tossed. The white gloves stayed in the drawer.
She became Jackie O.
This era was all about Valentino and Pucci. She started wearing oversized sunglasses (which she said she used to hide and watch people) and "gypsy" skirts. She’d pair a simple T-shirt with a $50,000 emerald necklace. It was effortless.
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One of her most famous later looks was her second wedding dress—a short, lace Valentino minidress in off-white. It was a total departure from the "First Lady" era. It was free. It was modern.
The Secret of the Pearls
You’ve seen the three-strand pearls in almost every photo.
They were fake.
She bought them at Bergdorf Goodman for about $35. She liked the way they looked, and she didn't care if they were "real." It’s a funny bit of irony—the woman who came from the highest society in America and lived in the White House was perfectly happy wearing costume jewelry.
How to Channel the Jackie Style Today
You don't need a vintage Chanel budget to pull this off. It's about the "math" of the outfit.
- Focus on the neckline: Look for bateau (boatneck) or square necks. They create a structured, "expensive" frame for your face.
- Monochrome is your friend: Jackie often wore one color from head to toe. It creates a long, lean line that looks intentional.
- The "Big Glasses" trick: It's not just for hiding. A large, dark frame adds instant mystery to a basic jeans-and-tee combo.
- Tailoring over trends: A $20 thrift store blazer looks like a $2,000 Cassini if the sleeves are the right length (just above the wrist bone).
If you’re looking to dive deeper into the technical side of her wardrobe, the John F. Kennedy Presidential Library and Museum has the best digital archives of her actual sketches and fabric swatches. It's worth a look if you want to see how much work actually went into looking "effortless."