the most stylish celebrities

A Look At The Most Stylish Celebrities Since The Year 2000

From the red carpet to the street, from music videos to stage performances, from concerts to festivals, the most stylish celebrities capture the world’s attention with their style, fashion choices and flair. 

In this blog article, we will look back through the lens of time to the most stylish celebrities since the year 2000

Why the year 2000 you ask?

I chose the year 2000 as a starting point because not only was it the turn of the millennium and the beginning of a new century, but it also introduced the era of the super celebrity.

The worldwide web, more commonly referred to as the Internet, was beginning to boom and with this expanded reach for entertainers and other industry creme de la creme, came superstardom.

For the first time in the history of the world, we could admire and draw inspiration from our favourite actors, musicians and entertainers from across the world. 

The world of fashion and style, like many other industries, benefited hugely from this global audience. Without further ado, here are the most stylish celebrities since the year 2000

Jennifer Aniston

Jennifer Aniston is an American actress, businesswoman and producer. 

Jennifer Aniston’s Rise To Fame

Jennifer Aniston rose to fame from her role as Rachel Green in a popular sitcom called “Friends” that aired on NBC from 1994 to 2004. 

Friends is a television comedy series about a group of friends living in New York, USA. 

Jennifer Aniston plays a runaway bride, who having abandoned her fiancé on the altar, goes about her life with her friends. 

The TV show focuses on the friend’s shared experiences including love, marriage, work and children. Do check it out sometime.

Jennifer Aniston’s Movies

Jennifer Aniston has also starred in several successful Hollywood movies including.

  • Bruce Almighty 
  • Derailed
  • Horrible Bosses
  • Bounty Hunter
  • The Breakup

To mention a few. 

Jennifer Aniston’s Style

Over the years Jennifer Aniston has cultivated a timeless and elegant style that has often been referred to as effortlessly chic.

In addition, Jennifer Aniston dresses in almost all styles and is therefore a good inspiration for the all-rounded fashion connoisseur. 

She loves classic tailored pieces, leggy dresses, jeans and t-shirts, wedges, necklaces, hats and sunglasses. 

With Jennifer Aniston, there is something for everyone. 

She is a woman we at The Stylefit can comfortably recommend as a fashion inspiration for any woman undecided on style.

Jennifer Aniston | The Most Stylish Celebrities
Jennifer Aniston | GETTY IMAGES

David Beckham

David Beckham is a former English professional footballer

In his day, he not only represented his national team England in many tournaments including the World Cup, but he also played for big European clubs like Manchester United, Real Madrid, AC Milan and PSG.

Right now, David Beckham is the president and co-owner of Inter Miami, a professional American soccer club based in Florida. 

David Beckham’s Rise To Fame

David Beckham began his professional football career at the age of 17 playing for Manchester United; 

Soon his distinct playing style on the right wing and his speciality at set pieces such as free kicks won him many admirers. 

He won several trophies while at Manchester United including six Premier League titles and one UEFA Champions League title

David Beckham then moved to Real Madrid and continued to cement his legacy.

He captained his national team for many years and is now seen as both a cultural icon and one of the greatest footballers to have ever lived. 

David Beckham In Fashion And Style

David Beckham has always been a lover of fashion.

He has managed to maintain a very flavorful, polished yet distinct look over the years.

His marriage to spice girl Victoria Beckham also elevated his position in the eyes of many fashionistas. Victoria Beckham is after all one of the best-dressed women in the world. 

She is also the founder of the fashion label Victoria by Victoria Beckham

David Beckham was already a fashion icon before he met and wedded Victoria but the marriage elevated both their fashion personas to a whole new level. 

David Beckham | The Most Stylish Celebrity
David Beckham | GETTY IMAGES

Rihanna

Rihanna is a singer, businesswoman, actress and fashion icon hailing from Barbados in the Caribbean. 

Rihanna’s Style 

Rihanna’s fashion style has continued to evolve from the days of “unfaithful” to her position now as the second richest musician in the world after JAY Z.

In addition, Rihanna now owns or co-owns influential fashion brands including; Savage X Fenty and Fenty Beauty. 

Being the CEO of these fashion brands no doubt contributes to her fashion sense. 

From edgy streetwear to glamorous haute couture, Rihanna fearlessly pushes fashion boundaries.

In addition, she is also a champion of fashion inclusivity and shuns traditional standards of beauty in her lingerie brand Savage X Fenty.

The brand has lingerie offerings for plus-size women, something most lingerie brands don’t do. 

Rihanna, the most stylish celebrities
Rihanna | GETTY IMAGES

Zendaya

Zendeya is an American actress and singer famous for her prodigious acting talent as well as her out-of-the-ordinary red-carpet looks.

Zendeya’s Style and Rise To Fame

Zendeya was an actor long before she made her debut on the big screens of Hollywood.

From 2010 to 2013, she starred as “Rocky Blue” in a Disney sitcom called “Shake It Up” 

The sitcom was a turning point in her acting career as it was here that her acting skills were broadcast for all to see. 

In 2013, she appeared as a contestant in ABC’s Dancing with the Stars where she acquitted herself surpassingly, becoming runners up in the final episode.  

Later on, she made several appearances in music videos for A-list musicians including Beyonce and Taylor Swift.

But her first big Hollywood role came when she starred as MJ in Spiderman 2017

Her cool, collected and elegant persona on the big screen drew fans to her in droves. 

In addition, Zendeya’s appearances on the red carpet for movie premiers and award shows dressed in bold pieces that effortlessly blend contemporary designs with old Hollywood glamour have cemented her cool-girl status and made her a darling of millions all over the world. 

Zendeya’s Biggest Films

If you are interested in seeing Zendeya at her best on the big screen.

Here are a few movies she is cast in. 

  1. Dune (2021)
  2. Spiderman – Homecoming (2017)
  3. Spiderman – Far from home (2019)
  4. Spiderman – No Way Home (2021)
  5. Smallfoot (2018)
Zendeya, the most stylish celebrities
Zendeya | GETTY IMAGES

Beyoncé

Beyoncé is an American singer, songwriter and businesswoman. 

Beyonce’s Style And Fashion Sense

Beyonce is probably the biggest name to come out of the pop music industry in the last century.

Few musicians are as evocative, as influential, or indeed as talented as Beyonce.

And less than few entertainers can hold a candle to her stage performances. She is a songstress unlike any the world has seen, or will see for many years to come.

Her songs can make you weep, jump in joy or brood in fomented distress. And her fashion sense is just as evocative. 

Beyonce is probably the biggest champion of women’s empowerment in the music industry, coining words like Diva – the female version of a hustler- and showing that women can stand for themselves and be leaders in their respective fields.

Her style is as varied as her vocal range, ranging from streetwear to hard-hitting red-carpet dresses.

Beyonce is an all-rounded fashionista. And that is understating the facts. 

Beyonce’s Biggest Songs

If you have been living under a rock and haven’t listened to Beyonce. 

Or if you have but don’t mind listening to a few great tunes from one of the most talented songstresses of all time, here are The Stylefit’s top five Beyonce hits. In no particular order.

  • Sweet dreams
  • Irreplaceable
  • Best thing I Never had 
  • Halo
  • Broken Hearted Girl
Beyonce, the most stylish celebrities
Beyonce | GETTY IMAGES

Ryan Gosling

Ryan Gosling is a Canadian actor. He is known for his impeccable acting in movies like Blade Runner 2049 and The Gray Man.

Ryan Gosling’s Style 

Away from the big screens, and when he is not being a lady’s man, in fashion circles Ryan Gosling’s name is synonymous with suave and sophistication. 

Ryan Gosling has mastered the art of clean lines and classic menswear. 

And more often than not, the pieces he chooses to rock come with a modern twist adding uniqueness and appeal to his overall look. 

And finally, his red carpet appearances for award shows and movie premiers are a lesson in refined masculinity. 

Ryan is without a doubt a fashion icon and we at The Stylefit heartily say he should serve as the standard and inspiration for any man looking to up his fashion and style game. 

Ryan Gosling’s Biggest Films

Over the years, Ryan Gosling has starred in many successful movies. Here are a few to sample in your free time.

  • The Gray Man
  • Blade Runner 2049
  • The Ides of March
  • First Man
Ryan Gosling, the most stylish celebrities
Ryan Gosling | GETTY IMAGES

Kate Middleton

Kate Middleton, now known as Catherine Princess Of Wales, following her marriage to William, Prince of Wales (heir apparent to the throne) is a member of the British royal family in the House of Windsor

Kate Middleton’s Style

It goes without saying that becoming a member of the British royal family skyrocketed Kate Middleton’s style to the attention of the world audience. 

But her fashion sense has always been part and parcel of her even before she joined the royal family by marriage. 

Catherine, Princess of Wales’s wardrobe is made of elegant, modest, and traditional silhouettes. As becoming a princess married to the heir of the British monarchy. 

In addition, Catherine, Princess Of Wales’s ability to mix high-end designer pieces with affordable fashion (or fashion pieces that appear affordable) has earned her many admirers. 

Kate Middleton, the most stylish celebrities
Catherine, Princess Of Wales | Courtesy of British Vogue

Lady Gaga

Lady Gaga is an American pop singer, songwriter and actress. 

Known for her bold and outrageous fashion pieces, her exhilarating music and her ability to continually reinvent herself in an industry where old is most often not considered gold.

Lady Gaga’s Style

Over the years, Lady Gaga has cemented solidly, her status as a fashion icon. 

No other female entertainer holds a candle to Lady Gaga’s red-carpet fashion pieces.

She has kept fashion pundits and fans alike guessing at what she is going to spot and she always goes beyond and above expectations every time.

At the 2010 MTV Music Videos Award show, Lady Gaga wore a meat dress, a literal dress made out of meat! 

And to the surprise of no one, the dress was bashed and condemned by Animal rights groups and at the same time declared the top fashion statement of 2010 by Time Magazine. 

An entertainer through and through, Lady Gaga will keep churning out the looks and we’ll keep appreciating them. 

Or at least the world of fashion will.

Lady Gaga, the most stylish celebrities
Lady Gaga | The Most Stylish Celebrities

Harry Styles

Harry Styles is an English singer. He rose to fame as a member of the boy band One Direction

The amazing thing about One Direction is it was formed by five former contestants of the British music competition The X Factor, each of whom had been eliminated at some stage of the competition. 

Being eliminated from the X Factor didn’t deter them from pursuing their dreams, and One Direction, their brainchild, has become one of the biggest boy bands of recent times. 

In 2023, Harry Styles just named the UK’s richest young star under 30 for the second year running with a net worth of a whopping 175 million Euros. 

Harry Styles’s Style

Harry Style likes his designer outfits. Most notably Gucci, Burberry and Siant Laurent. And who can blame him, a rich man needs rich habits.

His fashion sense is iconic, to say the least, whether he is spotting a fistful of rings or a pink suit, he is always pushing the bounds of fashion.

And doing so with grace and elegance; 

In 2018, Harry Styles’s position as a fashion icon was cemented when Gucci made him the face of their tailoring campaign.

And he has continued to inspire many while earning a gazillion fans worldwide with his music and his style. 

Harry Styles, the most stylish celebrity
Harry Styles | GETTY IMAGES

Summary

The new millennium has seen the rise of countless stylish celebrities who continue to raise the ceiling of fashion while influencing the way we dress.  

While Beyonce, Ryan Gosling, Lady Gaga, Harry Styles, Kate Middleton, David Beckham, Zendeya, Rihanna and Jeniffer Aniston are not the only stylish celebrities out there,

They are without a doubt a good representation of what fashionable celebrity looks like, and it’s potential to shape trends and inspire millions. 

Thank you for reading.

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