From 2006 to 2026—20 Celebrities Who Have Shaped the Last Two Decades
Believe it or not, Who What Wear has been around for 20 years, and we have plenty to showcase, particularly in the realm of celebrity fashion. Whether you've just started reading us or have been a loyal follower for years, you know we stay updated on the latest celebrity outfits. Over the last two decades, we’ve documented countless celebrity styles both on and off the red carpet, but there are a few who distinctly stand out for their influence, skillfully setting trends and sometimes launching their own brands or collaborations. To celebrate Who What Wear's 20th anniversary, we present our list of 20 remarkable celebrities who have shaped the past two decades. These actors, musicians, supermodels, and multifaceted talents have delivered numerous unforgettable style moments and have, in many ways, influenced what people worldwide wear. We're eager to see how their fashion evolves in the next twenty years.
Rihanna
Daring, striking, and innovative are words that capture Rihanna's style perfectly. There's a theatrical aspect expected from celebrities, especially musicians, and nobody meets this expectation quite like Rihanna. The unofficial queen of the Met Gala, she always makes a dramatic entrance on the red carpet, donning the most high-fashion outfit of the evening. In the late 2010s, Rihanna launched Fenty Beauty and expanded her brand to include fashion, demonstrating that she wields immense influence offstage as well.
Hailey Bieber
It's fair to say that Hailey Bieber has the ability to turn any outfit into an It item almost instantly and can make any trend she endorses go viral overnight. Her touch has influenced several brands over the years, showcasing her knack for selling anything. From creating a billion-dollar beauty label, Rhode, to collaborating with or representing brands like Miu Miu, Gap, Saint Laurent, Wardrobe.NYC, and Mango, her impact in today’s fashion scene is undeniable. Furthermore, she ranks among the most featured celebrities on modern Who What Wear.
Jennifer Lopez
If we had to describe Jennifer Lopez's fashion in one word, it would be glamorous, both at events and in casual settings. With her signature fur coats, towering heels, eye-catching designer bags, body-conscious pieces, and bold eyewear, she consistently captures attention. Even in more laid-back outfits like leggings and sneakers or Ugg boots, she turns heads. Her love for fashion is evident, and her eagerness to dress for any occasion is truly inspiring.
A$AP Rocky
A$AP Rocky's current style can be described as avant-garde, stylish, and retro. Over the years, his fashion has become more tailored, but he still incorporates elements from the streetwear-inspired looks he favored a decade ago. His fearless, gender-fluid aesthetic has made him the celebrity every brand desires to collaborate with and a style icon for fashion-forward men.
Jennifer Lawrence
There's no mistaking an It girl when you see one, and we're proud to say that Jennifer Lawrence was the subject of Who What Wear's very first editorial shoot back in 2010. She's transformed into a street style icon, often seen in chic off-duty looks that are effortlessly trendy. She uses color and playful accessories each season to infuse personality into her outfits, and her red carpet appearances are both elegant and unexpected.
Dua Lipa
Dua Lipa's fans admire her not only for her music but for her fashion sense as well. She embodies the ultimate fashionista, with each outfit sparking lively discussions online and setting off new trends. As a true pop star, she embraces eye-catching, trendy looks. Her status as a fashion icon was solidified when Matthieu Blazy designed an embellished, feather-accented wedding dress specifically for her.
Alexa Chung
For years, Alexa Chung’s whimsical and eclectic style has inspired many to emulate the chic British girl vibe. She was seen in baby-doll dresses paired with ballet flats and trench coats long before they became trendy. Chung has consistently remained true to her signature fashion while adapting to current trends, having launched a hugely popular collection with Madewell back in 2010 that was revived 15 years later to great excitement.
Sarah Jessica Parker
Since the debut of Sex and the City, Sarah Jessica Parker has been recognized as a fashion icon. Interestingly, she is celebrated equally for her own style as well as that of Carrie Bradshaw, the fashionista she portrayed for years. Together, they made the Fendi Baguette the It bag of the early 2000s (now reissued by Fendi) and helped make Manolo Blahnik a household name. Though Parker’s high-fashion outfits may not be universally accessible, she illustrated how to express individuality through fashion, emphasizing that it should ultimately be enjoyable.
Zendaya
There's no press tour quite like a Zendaya press tour. Working with Law Roach, her outfits for each tour are on-theme for the projects she is promoting, without appearing costume-like. Her looks for films such as Challengers drew
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From 2006 to 2026—20 Celebrities Who Have Shaped the Last Two Decades
They spark conversations and shape our fashion choices.
