Jackie Kennedy's Iconic 1960s Style

A-Line Dresses, Boxy Jackets and the Former First Lady's Signature Fashions

The “Jackie Look”

Jackie Kennedy, first official White House photograph, 1961. Mark Shaw/Underwood Archives/Getty Images

As first lady, Jacqueline Kennedy always looked sophisticated, young and chic. Soon after John F. Kennedy was elected president in November 1960, the 31-year-old began strategizing her Inauguration Day outfits and wardrobe as the nation’s new first lady. She sent numerous letters to her personal shopper in Bergdorf Goodman’s millinery department, Marita O’Connor, describing and sketching the hats and shoes she needed to accompany her custom-made outfits by American designer Oleg Cassini.

While Jackie loved French designers like Christian Dior, Balenciaga and Givenchy, she mostly wore Cassini’s American-made couture, which shaped the “Jackie Look” that American women emulated in droves.

“She’s the only first lady that’s been so well loved on every continent. She was like royalty,” said Steven Porterfield, an appraiser on PBS’s “Antiques Roadshow” and owner of The Cat’s Meow vintage store in Midland, Texas. “She worked really hard at it. She wasn’t a frivolous person; she was very brilliant. The reason her fashions are so popular is because of the type of person she was.”

Jackie’s Easy-to-Copy Style

Jackie and family
John F. Kennedy Presidential Library and Museum, Boston/Public Domain

Compared to the fashions of the 1950s that included large circle skirts and petticoats made of yards and yards of fabric, Jackie’s 1960s couture style was easier to imitate at affordable prices. Jackie’s look was minimal, modern, ladylike, and with pared-down accessories.

“She brought things into a simplicity that was easy to copy. It was more affordable to buy A-line dresses. You could be poor and still have a Jackie-style dress,” Porterfield said. “Her hats were simple little pillboxes instead of expensive couture designs. You could get a pillbox hat for $3.95.”

How to Dress Like Jackie Kennedy

Jackie Kennedy
John F. Kennedy Presidential Library and Museum, Boston/Public Domain

Fifty years later, women are still emulating Jackie Kennedy’s iconic first lady style. Many contemporary designers make A-line shift dresses and sheath dresses that evoke Jackie’s 1960s look. Plus, many vintage stores sell boxy jackets and trapeze coats from the 1960s at affordable prices.

Want to dress like Jackie? Shop for these eight signature fashion pieces that shaped Jackie’s standout style.

A-Line Dresses

Jackie Kennedy wears an A-line dress
Fotosearch/Getty Images

“A-line dresses are in again. You can find her look at most department stores,” Porterfield said. “A lot of her dresses don’t have a defined waistline. I think that was because she was so tall and thin and I think it made her look long and sleek.”

Jackie was reportedly 5 feet 9 inches tall; however, she often said she was 5 feet 7 inches tall. Porterfield estimates that Jackie wore a modern-size 4 or 6. If an A-line dress doesn’t complement your shape, accentuate your waist with a belt.

Boxy Jackets

Jackie In London
Jackie In London. 1962. Evening Standard / Getty Images

“Because she was tall enough to get away with it, she would wear boxy jackets with the very straight skirts,” Porterfield said. For petite women, try a boxy jacket with a short, slim skirt that will show off your legs and won’t overwhelm a small frame.

Solid Colors

Jackie in a pink gown
May 11, 1962. May 11, 1962/Apic/Getty Images

“She loved solid colors. If you look at her pictures, she very seldom wore a print,” Porterfield said. “Her favorite colors were pastels. She wore ivory, peaches, pale blues, yellows, pinks. You’ll see dark reds and brilliant blues and even a couple of dresses in bright chartreuse.”

Solid-colored dresses make a simple, elegant statement and are easier to style in multiple ways. Solid-colored separates are easy to mix and match. Plus, if you wear the right solid color, you’ll be sure to stand out in a crowd.

Matching Trapeze Coats

Kennedy Family in Rhode Island
Kennedy Family in Rhode Island, August 31, 1962. Bettmann / Getty Images

Jackie often wore trapeze coats in a solid color that matched her dress. Her coats were often free from adornment and featured large buttons covered in the coat’s fabric. Vintage stores are the best place to find bright trapeze coats. Look for knee-length coats with three-quarter sleeves.

Simple Jewelry

Jackie wears a blue gown with jewelry
John F. Kennedy Presidential Library and Museum, Boston/Public Domain

“One of her iconic looks was just a double strand (and also triple strand) of pearls. Nothing real gaudy,” Porterfield said. “If she wore a pin, it wasn’t really ostentatious. Not big, huge jewelry.” If you’re interested in wearing reproductions of Jackie’s favorite jewelry, check out the John F. Kennedy Presidential Library and Museum online gift shop or QVC’s Jacqueline Kennedy’s jewelry collection. The pieces are lovely and very affordable.

Low Heels

Jackie Kennedy's Shoes & Purse
Jackie Kennedy's shoes, clutches and sample shoe. Courtesy of John McInnis Auctioneers

Jackie, who wore around a size 10 or 10 ½ shoe, made flats trendy and popular.

“She wanted to be beautiful and elegant, but she also didn’t want to tower over diplomats who came from other countries, so she began wearing shorter heels,” Porterfield said.

In a letter written to her personal shopper Marita O’Connor in Bergdorf Goodman’s millinery department around December 1960, Jackie requests a pair of alligator shoes “size 10A—medium heel—slender—pointed toe but not too exaggerated—no tricky vamp business—usually I get Italian shoes at Eugenia of Florence—so you know the style I like—elegant and timeless."

Pillbox Hat

Jacqueline & John F. Kennedy
Mrs. Jacqueline Kennedy joins the President in greeting Ethiopian Emperor Haile Selassie at Union Station in 1963. Bettmann / Getty Images

“Her pillbox hat, everybody had to have that,” Porterfield said. Halston, who was a milliner in Bergdorf Goodman’s millinery department in the early 1960s, created Jackie’s iconic pillbox hat that she wore often, including on Inauguration Day in January 1960 and on November 22, 1963, with her pink Chanel suit when President Kennedy was assassinated in Dallas.

Big Black Sunglasses

Jackie in sunglasses, September, 1962
September 1962, Newport, R.I. September 1962, Newport, R.I./Kennedy Library Archives/Newsmakers/Getty Images

Everybody knows the oversized “Jackie O” sunglasses Jackie wore in the late '60s and '70s. But as first lady, she wore big black sunglasses while boating in Newport, R.I., and Hyannis, Mass. Black, slightly oversized oval sunglasses add a little glamour to any outfit.