The Fab Five – Icons of Fashion

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There is a long distinguished list of women who have left an indelible mark on the fashion world with their unique sense of style and sophistication. From a personal perspective, I have narrowed this list down to a small, but acclaimed group of women I refer to as the Fab Five, who were the ultimate ‘It’ girls of their time, but who continue to be admired by future generations. Their signature looks have captivated fashion editors, designers, photographers and stylists alike. Let me introduce to you, in no specific order, The Fab Five:

  • Grace Kelly, Her Serene Highness, Princess of Monaco
  • Audrey Hepburn
  • Marilyn Monroe
  • Jacqueline Kennedy-Onassis
  • Diana, Princess of Wales

Grace Kelly – Her Serene Highness, Princess of Monaco

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Grace Kelly was a screen goddess who embodied a regal sophistication. Her magnetism and allure intensified exponentially through her marriage to Prince Ranier of Monaco. Starring in iconic Alfred Hitchcock classics such as Dial M for Murder, Rear Window and To Catch a Thief, Kelly further established her status as Tinseltown elite with her Oscar winning Best Actress performance in Country Girl1.

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Her trademark demure look was characterised by classic and willowy silhouettes. ‘She did not flaunt. Even as a star, she would wear figure-hugging evening frocks but avoided overly revealing clothes. The waists were cinched, the skirts often full, the shoulders either bare or wispy with chiffon’2.

‘The leading costume designers of the time, including Edith Head (To Catch a Thief, Rear Window, and Dial M for Murder) and Helen Rose (High Society), played an integral role in developing the ”Grace Kelly Look” that swept across the globe in the mid-1950s’3.


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Audrey Hepburn

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Audrey Hepburn first captured the world’s attention with her breakout performance in Roman Holiday, which scored her the Best Actress Oscar4. Subsequent roles in Sabrina, Funny Face, My Fair Lady and Breakfast at Tiffany’s further cemented her status as one of Hollywood’s finest5.

Hepburn was gamine and boyishly slender. Her distinct facial structure, including the square jaw line, high cheekbones and immense doe-like brown eyes, epitomised a waif-like glamour and elfin beauty6.

 French designer Givenchy (to whom Audrey would become a muse) was influential in defining her professional and personal style7. Like Grace Kelly, Audrey’s trademark identity can be defined as understated, minimalist but elegant.



In fact, the Givenchy gown worn by Audrey’s character Holly Golightly in Breakfast at Tiffany’s has been voted the greatest outfit of all time, based on a survey conducted by Lovefilm8. In addition, the long white dress, hat and parasol costume Hepburn’s character Eliza Doolittle wore in My Fair Lady came in at number six9.


Marilyn Monroe



Marilyn Monroe is regarded as one of Hollywood’s ultimate femme fatales. As a star of Gentlemen Prefer Blondes, How to Marry a Millionaire, Some Like it Hot and The Seven Year Itch, Monroe oozed sexuality with a heady combination of sensual vulnerability.


Marilyn had a flirtatious smile with her pouty voluptuous lips, hypnotic eyes and a curvaceous body to match. However, behind the seductive, sultry, enigmatic façade, was an insecure individual10. Her public persona as the dumb blonde contrasted her true nature as an articulate, well read woman with a sharp wit, which only adds to her complex mystique11.


From a fashion perspective, Monroe preferred figure hugging attire that accentuated her hour-glass silhouette. ‘Her favourite costume designer was William Travilla, who created the iconic white billowing dress of The Seven Year Itch and the pink gown from Gentlemen Prefer Blondes. In a time of Peter Pan collars and poodle skirts, Marilyn’s style was considered risqué for her generation. This was exemplified by her tight dresses and suits, which flattered her shapely body and fitted like a glove’12.

Jacqueline Kennedy-Onassis


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Jacqueline Kennedy-Onassis was literally the First Lady to bring elegance and sophistication to the White House. From the moment John F. Kennedy was sworn in as President of the United States, the “Jackie Look” swept across America, and subsequently the world13.

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Jackie’s statuesque physique stood out along with her streamlined coats, A-Line dresses, pill box hats, white gloves and trademark bouffant hairdo.  ‘Oleg Cassini, a foremost fashion designer of the time, made the First Lady one of the best-dressed women in the world’ as the brains behind the “Jackie look”’14.


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In Cassini’s own words, ‘I wanted to dress her cleanly, architecturally, in style. I would use the most sumptuous fabrics in the purest interpretations’15. Her charm and intelligence, only added to her iconic persona. According to Cassini, ‘despite Jackie’s shy public presence and her whispery voice, privately she had a strong personality. Jackie’s taste was very simple – she liked only the very best’16.


Diana, Princess of Wales


At the height of her popularity, Diana, Princess of Wales, was the epitome of elegance and a jewel in the crown so to speak. Her impeccable poise, sophisticated regal ensembles, combined with her ability to break down barriers between aristocracy and the common man, set her apart from other royal members with their stand-offish formality.



Diana’s style transformation began during her ‘shy Di’ phase and continually evolved through to the final years of her life when she was crowned ‘the People’s Princess’, which reflected her ever increasing self-assurance and growing independence.


As Diana’s confidence bloomed, she took greater risks and became more experimental, making striking and bold fashion choices19. Diana’s wardrobe in her latter years was more daring, while maintaining a demure gracefulness. Furthermore, the heels got higher, clothes got edgier and skirts got shorter, both streamlined and flattering, while emphasising her figure. To further express her individuality, Diana favoured effortless minimal chic, which resonated in well structured and tailored shift dresses and pencil skirts, while gowns accentuated her slender and statuesque physique.

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For fifteen years, designer Catherine Walker played a significant role in developing Diana’s style identity20. Catherine understood that clothes were Diana’s mechanism to communicate the highs and lows of her life21. ‘Catherine found new ways for the Princess to win sympathy and support through her choice of clothes’22. ‘Dress by dress, look by look, phase by phase, Diana illustrated the story of her life’23.

The Fab Five were fashion forward trendsetters, who occasionally broke the rules to create their own signature look that reflected their individuality and own personality. Poise, elegance, glamour, classic and timeless beauty are terms synonymous with each of these women. Each still possess something inspirational to women of today, as the French would say – je ne sais quois. A distinct, intangible quality is the source of their enduring appeal. Their ultimate legacy is one of beauty, grace and charm. Even years after their death, we will continue to be captivated by their elusive mystique.

Citation Reference List – On Request

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46 thoughts on “The Fab Five – Icons of Fashion

  1. Hi, thanks for stopping by and liking my blog. Of course I had to visit you and I love your site. I think I would rather read your blog than the daily news. Just loved “The Fab Five – Icons of Fashion”. You have my 5 favourite women of all time. Each one of them not only a success in their own right, but also they have left incredible memories for women worldwide (well at least in my age bracket :)). Have a great day and I look forward to visiting your site some more.

  2. Absolutely fascinating read. Very well done. I just finished reading ‘Killing Kennedy’. Interesting you have Marilyn Monroe back to back with Jackie Kennedy. Maybe its my imagination running overtime.

    • Thank you so much. I think this post was my 3rd attempt, still at my early stage of blogging. I too i’m fascinated with the Kennedy clan, I have a few books of my own that I’ve read. I had the same thought when I put Jackie & Marilyn together. I guess JFK had good taste in women?? hahaha

  3. Lovely pictures, gorgeous women.

    Eighteen years ago, when I studied in London, I went shopping on Kensington High St one midweek afternoon. I heard lots of hushed whispers, turned and saw Princess Di was walking down the street, seemingly alone. Amazing moment.

  4. I agree with your choice. They are beautiful aren’t they and Princess Diana was a real icon of mine. A real princess inside and out. Her triumph was that so many women loved her, identified with her, lived her life vicariously with all its ups and downs.

    What struck me in your choice though was what tragic lives at least four of the five led. I don’t know much about Audrey Hepburn, so hopefully she was the exception to the rule, but never the less the tragic lives led by 4 out of 5 is statistically depressing. It doesn’t suggest that their outstanding beauty brought them much personal happiness does it?

    • Princess Di is definitely an icon. I love the fact she broke down barriers and helped so many people through various charity work. It is ironic that despite their beauty, their life was filled with ups and downs. I think that’s why they’re even more fascinating.

  5. Love this! They are my favorites too. I love your blog and will start following you. I just started blogging and I know I can learn a lot from you… and thanks for visiting my blog too!

    • These women are timeless….absolutely iconic! I’m so glad you like my blog. That means so much to me. Blogging is a passion of mine. It’s so much fun to write about topics you love and enjoy.

  6. This was such an amazing read. I must say I better be a regular at your blogs in order to understand the nuances of the fashion world better. Just fascinating.

    • I must admit this is one of my most read posts. I wanted to be a fashion designer when I was little…sadly, my drawing skills were terrible. But I’m a huge fan of these fashion icons.

  7. Hi there, really enjoyed this post! They are indeed five fashionable and elegant women that were chosen. I’m just curious, were these five particular women chosen because of personal taste or was it intended to be a post about style icons generally? It’s gotten me thinking about who my style icons would be!!

    • Hi! Thanks so much for reading my post. I’m so glad you enjoyed it. The Fab 5 were chosen for both their personal taste and being style icons in general. These women have this timeless elegance.

  8. Pingback: The Fab Five – Icons of Fashion | THE VIBE 101

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