For many women, deciding what to wear is a difficult decision. Nothing in your closet seems to bring you joy, but the idea of trekking to the mall and finding something there instantly ruins your mood. Don’t you just wish you could go back to a time when fashion seemed easy, and all the women we saw on TV and in the news were so effortlessly elegant and glamorous?
From Elizabeth Taylor to Princess Diana, our favorite fashion icons continue to inspire us with their impeccable taste. And style aside, let’s not forget that many of these ladies weren’t afraid to break with tradition. Though their outfits are what we remember most, these women were able to accomplish a great many things — like working tirelessly as humanitarians — all while looking fabulous.
“Over the years I have learned that what is important in a dress is the woman who’s wearing it,” fashion designer Yves Saint Laurent once said — and these next eight women prove his point. Let’s take a look back at the women who wowed us with their grace, elegance, and confidence over the last 80 years — and the gorgeous outfits they wore while doing it.
Keep scrolling to see our favorite fashion icons of all time.
Fashion Icons Of All Time Bette Davis Style
1940s; Bette Davis
Bette Davis cultivated her love for performing at a young age, appearing in several theater productions during the years she was in school. Fun fact: She and Lucille Ball were even classmates at the John Murray Anderson/Robert Milton School of Theatre and Dance. Davis eventually transitioned to Hollywood, where she would go on to become one of the most renowned leading ladies. Davis is best remembered for her long list of acting credits, which include Dark Victory, All About Eve, and What Ever Happened to Baby Jane?, as well as her famous feud with Joan Crawford.
In the 1940s, women's fashion trends were utilitarian due to the rationing of fabrics during World War II. Square shoulders, narrow waists, and skirts that fell right below the knee were popular styles. Despite the hardships during this decade, Davis found a way to maintain the glitz and glamour of Hollywood with her look. Her famous "Bette Davis' eyes" — a stunning bright blue — sparkled against the pale blue hue of her dresses, and it was rare to catch her without perfectly done red lipstick.
Fashion Icons Of All Time Elizabeth Taylor Fashion
1950s; Elizabeth Taylor
Elizabeth Taylor was a star from a young age, starting as a child actress in the 1940s. Her breakthrough role came when she was cast as Velvet Brown in the MGM film National Velvet. She transitioned into adult roles in the '50s and '60s, starring in the the film adaptations of the plays Cat on a Hot Tin Roof and Suddenly Last Summer. Later, she famously went on to act in the blockbuster Cleopatra, where she met her future husband Richard Burton. Though her acting accomplishments are often overshadowed by her many husbands, Taylor was a star in her own right.
It's hard to think of a bigger 1950s fashion icon than Elizabeth Taylor who sported the decade's popular trends: bullet bras over tight sweaters, full skirts, floral prints, and sultry red lipstick. She also happened to be the owner of a very enviable collection of dazzling sparklers and gemstones. Elizabeth Taylor's jewel collection includes a 33.19-carat Krupp Diamond ring given to her by Burton and a heart pendant from her third husband, Mike Todd, which she wore to her wedding to Eddie Fisher.
Fashion Icons Of All Time Jackie Kennedy Style
1960s; Jackie Kennedy
Former first lady and ultimate style icon Jackie Kennedy exuded grace and sophistication. During her first marriage to JFK, Jackie epitomized class with her pillbox hats, colorful-yet-tasteful suits, and sleek bouffant hairstyle. After her husband's assassination and her subsequent marriage to Greek shipping magnate Aristotle Onassis, the newly dubbed Jackie O was known for her oversized sunglasses and beautiful silk scarves and head wraps.
Though Jackie Kennedy's style continues to influence fashion even today, we shouldn't forget the other ways in which she honored the Kennedy family name. "I feel so fortunate to have had such [a] great role model...as a mother and a woman," her daughter Caroline said.
Fashion Icons Of All Time Cher Outfits
It's hard to think of a bigger fashion icon in the music industry than Cher. A talented singer and actress, she and husband Sonny Bono formed one of the most beloved husband-wife singing duos of all time. When the pair landed their show The Sonny & Cher Comedy Hour, it was Cher's over-the-top outfits that elevated her to not only TV star but global trendsetter as well.
During the 1970s, Cher had fashion designer and costumer Bob Mackie to thank for her fashion-forward wardrobe. The friends collaborated throughout the decade on many of Cher's most memorable outfits, including the Swarovski crystal-embellished fringe sheer gown she wore to the Met Gala in 1974. To this day, the two work together closely, with Mackie designing Cher's outfits for her Vegas residency. "She’s never been intimidated by the outfits," Mackie said of his famous friend. "She walks out, and there she is!"
Fashion Icons Of All Time Princess Diana Style
1980s; Princess Diana
Princess Diana — "The People's Princess" — was as beloved for her fashion as she was for the warm and caring way she lived her life. Though our embarrassing '80s photos make us cringe, old pictures of Princess Diana's outfits never look dated. Only she can make us miss the decade's big hair, shoulder pads so large you could launch a rocket from them, and tailored suits in eye-searingly bright colors.
But Princess Diana's legacy, and much of her fashion sense, has been carried on through not only her boys, Prince William and Prince Harry, but also the daughter-in-law she never got to meet. Kate Middleton channels Princess Diana's style consistently and beautifully — ensuring that somewhere, somehow, Diana is smiling proudly.
Fashion Icons Of All Time Cindy Crawford Style
1990s; Cindy Crawford
The 1980s brought us the advent of the supermodel, an idea that continued into the '90s with perhaps the most famous supermodel of all time: Cindy Crawford. Slinky silk dresses, lip liner with brown lipstick, and chunky sandals were the trends of the day, and Crawford pulled them off with ease.
For years before she became a household name, Cindy found her signature beauty mark to be a source of embarrassment. In her book Becoming Cindy Crawford ($27.99, Amazon), she wrote that she was often teased for it. "Hey, little Crawford, you have chocolate on your face!" the boys would scream. She begged her mother to let her have it removed, but her mom's attitude was, "You know what your mole looks like. You don’t know what a scar will look like." After Crawford's face began to grace the covers of magazines — with her beauty mark front and center — she eventually learned to embrace her natural beauty.
Fashion Icons Of All Time Cate Blanchett Style
2000s; Cate Blanchett
No one is as consistent as actress Cate Blanchett when it comes to stunning red-carpet gowns — even when pregnant! During the 2000s, Blanchett gave birth to three sons and appeared in the Lord of the Rings franchise, The Aviator, Babel, Indiana Jones and the Kingdom of the Crystal Skull, and The Curious Case of Benjamin Button among others, so she had many opportunities to stun in designer looks. (Her fourth child, a daughter, was adopted in 2015.) For her work, she has been nominated for hundreds — literally — of awards, including seven Oscars and nine Golden Globes. And considering she always makes our best-dressed list, it's safe to say her sartorial sense is as dominant as her prominence in Hollywood.
“She’s considered a risk-taker, but I don’t think she views it that way," her stylist Elizabeth Stewart told In Style. "She wears what she is drawn to, and her natural taste leans toward the quirky and sophisticated.”
Fashion Icons Of All Time Christie Brinkley Now
2010s; Christie Brinkley
Model and actress Christie Brinkley first shot to stardom in the late '70s and early '80s thanks to her Sports Illustrated: Swimsuit covers. In addition to her highly publicized marriages, Brinkley has become a humanitarian, campaigning for human and animal rights.
Now in her 60s, Brinkley still maintains the long, luscious blonde hair and statuesque figure that made her famous, and she certainly isn't worried about dressing "age-appropriate" (whatever that means!). Cute mini dresses, sleek jumpsuits, bold colors, and even bangs — Brinkley makes everything look fabulous!