Top 15 Biggest Fashion Icons Of All Time

Fashion, Lists

There are many fads within fashion that fade in and out over time. While something like the little black dress is a timeless piece that has lasted and remained a classic for ages, the parachute pants of the late 1970’s is something most people prefer to forget about. With each new fashion comes a new icon of fashion, usually a graceful and classy person represents the fashion and acts as a muse to many fashion designers, such as Oscar de la Renta and Hubert de Givenchy. Some fashion designers felt so inspired by celebrities that they created pieces specifically to be worn by them.

The following is a list of some of the most timeless and biggest fashion icons of all time.


Twiggy, also known as Lesley Lawson, is an English model, singer, and actress, was the world’s first supermodel and was a prominent icon and representation for the mid 1960’s swinging sixties London. She was famously referred to as Twiggy due to her thin build and her very large eyes, beautiful long eyelashes, and short hair. She modeled all over the world for numerous high end fashion designers and was featured on the covers of Vogue and other prominent fashion magazines. Twiggy was also named “The Face of 1966” by The Daily Express. Her photograph was put into a time capsule that was sent into outer space, and made the ‘Twiggy dresses’ famous. Twiggy retired from modeling in the 1970’s, but continued to be a very prominent figure in the world of fashion. She has made numerous appearances on shows like America’s Next Top Model as a panel judge, and posed with David Bowie for the cover of his Pin Ups album. She currently runs advertising campaigns with Marks and Spencer.


The very well known pop singer, actress, and model Madonna has captured all different types of styles and fashions effortlessly, going from one trend to the next without hiccups. She is known for constantly reinventing herself ever since her first appearance on the scene in the 1980’s with her fishnet stockings, lace bras, bleached blonde hair, and gaudy jewelry. Madonna has influenced not only the fashion world, but also celebrities such as Lady Gaga and Rihanna. With more diverse looks and styles that anyone else, Madonna is unapologetic about it all. She eventually tailored her look to be less provocative and more old school glamour of Hollywood circa 1930’s. When recently counted, Madonna has had well over 25 transformations, possibly more, with her fashion sense and style. It will be interesting to see how many more transformations she may undergo before finally settling on a look for good, but then again, Madonna will continue to amaze us.

Audrey Hepburn

Beautiful actress and human rights activist Audrey Hepburn has captured the heart of fashion lovers and designers around the globe. She is the embodiment of classy and sophisticated, all while still appearing to be mysterious and kind. Audrey Hepburn was a muse to many well known fashion designers with the likes of Issac Mizrahi, Hubert de Givenchy, and Salvatore Ferragamo. She was referred to as unique, angelic, calm, and truly kind by many of the actors and directors that she worked with. Even after her death, she remains the most influential style icon of all time. Audrey Hepburn continues to influence people and stars such as the Olsen Twins and Johnny Depp who happily name her their major fashion influence. When she gained a lot of fame during the height of her career, Audrey Hepburn would always laugh when people said she was beautiful because she would call herself just another skinny broad. A beautiful woman indeed, and one of the most stylish women that have ever lived.

Michael Jackson

Throughout his career as the King of Pop music, Michael Jackson was one of the biggest male fashion icons to date. His most famous and well known fashion accessory, for which he became known for, was his one glove. He also donned the red jacket for a while before transitioning over to military jackets and face masks. His style was expensive and exceptionally glitzy, for he had a love of embellished jackets and loud accessories. Big stars such as Beyoncé and Kanye West have been majorly influenced by his fashion and style. His fashion tending to change with the times, though he always made the classic fedoras and loafers look perfectly put together with his ankle length pants. SInger Chris Brown was most influenced by Michael Jackson’s signature red jacket, donning one of his own, and eventually adding glitz and glamour to his own wardrobe.

Naomi Campbell

Naomi Campbell was the first black woman on the covers of British and French Vogue and is a well known supermodel that has influenced generations of women throughout her career. She was also the first black model on the cover of Time magazine. Known for her extremely long legs and beautiful profile face, she quickly became a fashion icon for big fashion labels such as Ralph Lauren and Francois Nars. Despite a temper that has gotten her in trouble with law enforcement several times, she would redeem herself and come back stronger than ever from a fall. She has influenced celebrities such as Usher, Mike Tyson, and Flavio Briatore, and work with Nelson Mandela from 1997 until closer to his death. Naomi Campbell’s style was influenced by the likes of Coretta Scott King and was always classy and well put together. She is also known for doing more risqué photo shoots for magazines like Playboy and also modeled for Madonna’s book ‘Sex’.

Princess Diana

Under constant scrutiny from the media and press, Princess Diana was an unbelievable elegant and glamorous fashion icon and person. Unlike many celebrities, Princess Diana took complete control of what she wanted to wear and how she wanted to be perceived and shown in the public eye. Princess Diana was also credited for reviving the British fashion industry, and declared that clothes were part of her charisma as well as just being her own person. In the early 1980’s, people around the world were already becoming hugely influenced by Princess Diana’s look and sense of style. Many people sought to have her hairstyle and similar clothing pieces to replicate her tasteful and timeless look. She also influenced the making of what was known as ‘Lady Di’ blouses that sold faster than many pieces at the time. Years after her untimely death, people continue to be influenced by her style, including the current Royal family. Princess Diana was the epitome of elegance, and face of Marks and Spencer for many years.

Michelle Obama

One of the most influential fashion icons of today is First Lady of the United States Michelle Obama. Always dressed to impress, usually donning timeless staples and beautiful, rich colors, Michelle Obama quickly became a fashion icon, stressed the importance of mentoring and helping military families, and became an advocate for fighting childhood obesity in the United States. Michelle Obama’s style is classic and sophisticated, similar to a well known former First Lady, Jackie Kennedy, yet still has a style all of her own. Dressing right for every occasion, Michelle Obama loves to use statement pieces to represent a mood or an event that she is going to. For an inaugural ball, she wore a striking red chiffon and velvet gown that symbolized her patriotism. She has been a major fashion icon and influence for many women and celebrities, and continues to be a First Lady with an unbelievable about of class and style.

Jacqueline Kennedy Onassis

Former First Lady of the United States, Jackie Kennedy, was an iconic symbol of fashion, always chic and made dressing in style seem effortless. She was a fan of imitating art through her fashion choices, and loved to wear high end designer clothing from Coco Chanel, Givenchy, and Christian Dior. The looks she is most well known for that many women imitated and were influenced by were her use of A-line dresses, pillbox hats, and pastel blouses and suits. Throughout the 70’s, her style evolved into wearing more separates such as shirts and trousers, while also wearing oversized sunglasses. She was America’s most stylish woman all the way until her death in 1994. When designers look to the 1960’s and 1970’s for inspiration, she is one of the main people that are looked upon to recreate or revive an older, classic style. Jackie Onassis continues to be an inspirational fashion icon.

Bettie Page

Well known for her sex appeal and lack of inhibition in front of the camera, Bettie Page was a symbol of fashion in the 1950’s, with blue eyes and jet black hair. As a pin-up model, she loved shocking the public with crazy photo shoots that dove into the world of submission behind closed doors, becoming a goddess among the bad-girl look of fashion. She was also one of Playboy’s first Playmates in January of 1955. By the 1960’s, Bettie Page left the world of fashion photography to become a born-again Christian and to live an anonymous life. In the 1980’s, women revived her trademark style, admiring her pin-up status and wanting to bring that style back to life. Bettie Page then re-emerged into the spotlight to help make famous her trademark style again, as well as help sell products for profit. She will always be remembered as the queen of pin-ups.

James Dean

A handsome actor that died way too soon at the age of 24, James Dean was and has remained a timeless style icon from the 1950’s. With the look of a rebel and a smile that melted women’s hearts, James Dean was solely responsible for the fashion change of old Hollywood that caused fashion to dress down. Though James Dean did not aim to change the overall style of Hollywood, it was something that happened without his control, and his confidence radiated through to his fans. Perfectly capturing the look of casual cool, James Dean would never overdress, and always pulled off every look he ever tried. His most famous look was his use of grey wool trousers that just recently took off in the fashion world. He refused to wear anything that was ostentatious or distracting, which said a lot about his character. James Dean remains one of the effortless fashion icons of all time.

Andy Warhol

Andy Warhol is most famously known for his Pop art influenced work and making the ‘Factory Girl’ look popular, he was a fashion icon that loved to shock people with his bright accessories and tattered suit jackets. Andy Warhol not only influenced men with his fashion, but he influenced a tremendous amount of women with his style, using his muse Edie Sedgwick to showcase his famous factory girl look which consisted of smoky eye makeup, big and bright accessories, short hem lines, statement pieces, and black and white motifs. Warhol was famous for saying that fashion was something that was not for wearing some place, but that fashion was the whole reason for going. His work continues to inspire many fashion designers around the world and people looking to change up their style, and will continue to be an influence not just in fashion, but also in the world of art.

Farrah Fawcett

Her most well known attribute being her voluminous curled hair, Farrah Fawcett was the supreme fashion icon of the 1970’s retro era. Starring as a private investigator named Jill Munroe on the famous television show Charlie’s Angels, she quickly made her fashion and style, from her hair to her clothes, the must have look of the late 1970’s. The actress made famous by through her hairstyle, dubbed the Farrah Flick, became the first must have celebrity hairstyle. Her clothing, on the other hand, is what really made her become one of the biggest fashion icons of all times. She was well known as a sex kitten for often going without bras and wearing high waisted demin flared jeans. Her most famous and best selling photograph was a pin-up of her in a red bathing suit with her head and hair thrown back behind her. Farrah Fawcett was a symbol of femininity and confidence, making way for major changes in fashion by the time the 1980’s came around.

Bob Dylan

Bob Dylan was a famous musician who brought a new sense of confidence to fashion when he came onto the scene in the 1960’s. He started off in the music world with a folk and blues sound, and his style followed suit with classic flannel pieces and blue jeans, occasionally wearing an engineer’s cap to top of his look. After becoming a well known folk musician, Bob Dylan decided to change up his music and his look, heading down the road of rock and roll. Once he changed up his music style, he left flannel and jeans behind, in place of them wearing fitted pea coats, polka dot shirts, fitted trousers and jeans, and scarves. His style quickly became popular for designers creating new lines to keep up with the times, and give fashion a more chic appearance. Bob Dylan proved that even in short amount of time, you can always reinvent yourself and keep things interesting.

Lady Gaga

Notoriously known for her outrageously loud and colorful style, Lady Gaga breaks all of the rules of fashion and pushes the boundaries with her style choices. From wearing outfits that were made of raw meat, to wearing plastic bubbles, Lady Gaga relies on shocking her fan base in order to make a fashion statement. Donning wigs, scarves, feathers, large, asymmetrical shapes, and even sporting a Kermit the Frog look, Lady Gaga continues to bend the mold and push her way out of her comfort zone in the name of fashion. Lady Gaga has worked with numerous famous high end designers including Giorgia Armani for outfits for her tours, and has even worked with V Magazine to write fashion columns. Madonna is one of Lady Gaga’s fashion influences, and she plans to continuing shocking people with her fashion and will be a fashion icon for many years to come, we’ll be waiting to see what’s next.

Steve McQueen

Famously known as “The King of Cool”, actor Steve McQueen was a master of cool and taking the All American look, turning it into a rebellious rugged look that matched perfectly with his no-nonsense personality. Passionate about racing cars and motorcycles, he embodied perfectly the rebel masculine look that many men desired to imitate through fashion. Steve McQueen was well known for his famous aviators, tailored suits and sport coats, V-neck sweaters, racing jackets, and lots of denim. He influenced many designers, including Rolex, who named a Explorer watch after him. He was the first man to appear on the cover of Haper’s Bazzar, Steve McQueen loved to dress down in jeans and yet still pulled off an extremely sophisticated look. Even with a rugged look, Steve McQueen made sure all of his shirts and clothes fit well, which is what made his style so classy and replicated even today.