Jackie Kennedy's Iconic 1960s Style

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

Jackie Kennedy

Bettmann / Contributor / Getty Images

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. Jackie’s look was minimal, modern, ladylike, and with pared-down accessories. But perhaps the best part about Jackie Kennedy's style was that anyone from any fashion budget could achieve it. "You could be poor and still have a Jackie-style dress," says Steven Porterfield, an appraiser on PBS’s “Antiques Roadshow” and owner of The Cat’s Meow vintage store in Midland, Texas. “She brought things into a simplicity that was easy to copy. “Her hats were simple little pillboxes instead of expensive couture designs." (FYI: You could get a pillbox hat for $3.95.)

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? Keep scrolling to learn the must-haves that shaped Jackie’s standout style.

The “Jackie Look”

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

If there's one thing everyone (from her era or not) can agree on, 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 (talk about getting ahead of the game). 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,” says Porterfield. “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.”

A-Line Dresses

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

Good news for A-line dress lovers: not only are they in again, but Porterfield says that a lot of Jackie's dresses didn'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," he notes.

A-line dresses are great for lengthening the body (aka they're slimming) and taking attention off the mid-section. If you feel like an A-line dress doesn’t complement your shape, you can accentuate your waist with a belt.

Boxy Jackets

Boxy jackets

Getty Images / Staff

“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, and make for an easy, no-fuss outfit that requires little to no thinking.

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. Looking to add a trapeze coat to your wardrobe? Vintage stores are your best bet. Look for knee-length coats with three-quarter sleeves to really nail the Jackie look.

Simple Jewelry


Bettmann / Contributor / Getty Images

When it came to jewelry, nothing she wore was gaudy or over the top—if she wore a pin, it wasn’t really ostentatious. One of Jackie's iconic looks was donning just a double strand (and also triple strand) of pearls. For a modern take on the classic pearl, opt for a pearl ring (we're digging Starlette Galleria's Infinity Pearl Ring, $60).

Low Heels

Low heel

Independent News and Media
 / Contributor / Getty Images

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 was something everybody had to have, according to Porterfield. 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 1963 with a 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.