9 Biggest Fashion Icons Of All Time

Published on June 1, 2015. Updated April 3, 2017

Hollywood is a pretty fashionable place. Basically everyone can afford designer brands; however, just because they can afford good fashion doesn’t mean that they know how to wear it. Fashion is a really delicate thing, as we’ve seen time and time again. Some people know how to wear it and they make it look pretty effortless. Other people just can’t seem to pull it off. They don’t get fashion and it doesn’t work on them either. Today, we are looking at the biggest fashion icons of all time. Some of these fashionable celebrities made their mark a long, long time ago while others are still around, pushing boundaries and establishing new trends.

9. Zelda Fitzgerald

Zelda Fitzgerald was married to the writer F. Scott Fitzgerald. She was considered the “first Flapper” and came to epitomize the Roaring Twenties with her short hair, short dresses and her penchant for drinking and drama. She inspired fashion as much as she inspired much of her husband’s writing.


8. Audrey Hepburn

Audrey Hepburn will always be one of the top fashion icons because we are still influenced by her sense of style today. Many of the pieces she wore are still popular, like fitted pants, little black dresses and cropped silhouettes. One of the reasons fashion just worked on her was because of her confidence. She was comfortable in her skin, which is the best accessory one can wear with their clothes.

7. Twiggy

Twiggy – real name Lesley Lawson – was one of the first international supermodels and one of the big style icons of the 1960s. She changed fashion and modeling with her androgynous waif-like look and helped to popularize mode fashion, which included trends like miniskirts, bold colors and prints, and hot pants.


6. Jacqueline Kennedy Onassis

Jacqueline Kennedy Onassis is easily one of the best dressed women of all time, which is why she has gone down in history as one of the ultimate style icons. She was famous for her fitted jackets, sleeveless A-line dresses, above-the-elbow gloves, low-heel pumps and famous pillbox hats, which were all simple, but stylish.


5. Debbie Harry

Debbie Harry wasn’t just a punk icon – she was also a fashion icon because of her unique sense of style, which can be characterized as both edgy and feminine. She wore everything from biker leathers to leggings to funky maxis to leopard print to glamorous catsuits.

Photo by Andre Csillag / Rex Features

4. Madonna

When Madonna first exploded onto the pop scene in the ‘80s, she quickly established herself as a fashion icon. With her fishnet leggings, mini skirts, crop tops and loads of accessories, she had quite the look. Since she first rose to fame, she has proven herself to be quite the style chameleon. With each album, she seems to change her look. Even in her 50s, she’s still pushing the envelope with her fashion.

Credit: Photo by ITV/REX

3. Princess Diana

Princess Diana had impeccable style, which captivated the world. When she first married Prince Charles, her clothes were more dowdy or demure; however, as her confidence grew, she started to take more risks and push more boundaries. Her style became decidedly more elegant and glamorous and, at times, daring.

Mirrorpix/Courtesy Everett Collection

2. Kate Moss

Kate Moss has ruled the fashion industry since the early ‘90s when she first rose to fame as part of the heroin chic fashion trend. Only 5’7” with a waifish frame, she was the anti-supermodel. Somehow, in spite of her limitations, she has ruled the fashion industry for close to 25 years. Her style has influenced designers like John Galliano, Marc Jacobs and Vivienne Westwood, as well as stylists and buyers at retail stores.

Photo by Jerome Domine/ABACAPRESS.COM

1. Kate Middleton

Kate Middleton is more of a reluctant style icon. She was thrust into the spotlight when she started dating Prince William and, since that fateful day, the world has been obsessed with her sense of style, which has really evolved since she wed her university sweetheart. She is best known for mixing high street and designer brands. Whatever she wears, she always looks comfortable but elegant.

Photo by Rex Features
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