From 2006 to 2026—the 20 Celebrities Who Have Defined the Past Two Decades
Read all about the influential figures who are as stylish as they are talented.
Believe it or not, it's been 20 years since Who What Wear came to be, and we have a lot to show for it, especially in the arena of celebrity style. Whether you've been a reader of ours for years or weeks, you know that we have our finger on the pulse of what celebrities are wearing at any given moment. Over the past two decades, we've covered countless celebrity looks on the red carpet and off, but there are a select few that truly stand out for being the most influential and dictating what's cool, wordlessly deciding which trends will take off, and sometimes even launching their own brands or collaborations.
In celebration of Who What Wear's 20th anniversary, we invite you to peruse our list of the 20 multitalented celebrities who have defined the past 20 years. These actors, musicians, supermodels, and multi-hyphenates have had numerous memorable style moments over the years and, in many ways, shaped what people around the world wear. We can't wait to see how their style evolves over the next two decades.
Rihanna
Risk-taking, bold, experimental—they're all words that sum up Rihanna's style. There's a theatrical element that we expect from celebrities—especially musicians—and no one fills that expectation better than Rihanna. She's the unofficial queen of the Met Gala, always arriving on the red carpet at the eleventh hour wearing the most dramatic, high-fashion look of the night. In the late 2010s, Rihanna started Fenty Beauty, along with a fashion arm of the brand, proving that the entrepreneur is as influential off the stage as she is on.
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Hailey Bieber
It's safe to say that Hailey Bieber can turn anything she wears into an It item in an instant and can make any trend she endorses go viral overnight. She's touched many brands over the years, routinely proving that she can sell anything. From creating a $1 billion beauty brand in Rhode to collaborating with or serving as an ambassador to brands such as Miu Miu, Gap, Saint Laurent, Wardrobe.NYC, and Mango, her influence in the modern-day fashion world is apparent. Not only that, but also she's one of the most-covered celebrities of modern-day Who What Wear.
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Jennifer Lopez
If we had to sum up Jennifer Lopez's style in one word, it would be glamorous—both on the red carpet and off. Fur coats, sky-high heels, statement-making designer bags, body-con pieces, and dramatic eyewear are some of her trademarks. Even when wearing leggings and sneakers or Ugg boots for casual outings, she turns heads. It's easy to see how much she loves fashion and that she enjoys getting dressed for every occasion, which is inspiring to say the least.
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A$AP Rocky
Avant-garde, dapper, and retro is how we'd describe A$AP Rocky's present-day style. His aesthetic has evolved over the years, becoming more tailored, but he still seamlessly incorporates elements of the streetwear-inspired looks he primarily favored a decade ago. His fearless, gender-fluid style has made him the celebrity every brand wants to work with and every fashion-minded guy wants to dress like.
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Jennifer Lawrence
We know an It girl when we see one. We're proud to say that Jennifer Lawrence was the subject of Who What Wear's very first editorial shoot in 2010 and equally proud to see the street style icon she's become. She's regularly spotted on the streets of downtown NYC wearing chic off-duty looks that are trend-forward in the most laid-back of ways. In every season, she uses color and playful accessories to add personality to her looks. Her red carpet looks are elegant yet cool and unexpected.
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Dua Lipa
Fans of Dua Lipa admire her as much for her style as they do her music. She's the fashion person's fashion girl. Everything she wears is breathlessly discussed across the internet and launches one trend after another. Like a true pop star, she never shies away from attention-grabbing, trendy looks. Not only that, but you know you're an A-list fashion icon of our time when Matthieu Blazy designs an embellished, feather-dusted wedding dress for you.
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Alexa Chung
Alexa Chung's whimsical, eclectic style has been making us all want to dress like a cool British girl such as herself for years. She was wearing baby-doll dresses with ballet flats and trench coats long before everyone else was. Chung has always stayed true to her signature style while still evolving to embrace current trends. The first of her wildly popular collections with Madewell launched way back in 2010 and was resurrected 15 years later to equal fervor.
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Sarah Jessica Parker
From the day Sex and the City premiered, Sarah Jessica Parker became a fashion icon. What's interesting is that she's equally admired for her personal style as that of Carrie Bradshaw, the fashion-obsessed writer she portrayed for so many years. Both Parker and Bradshaw made the Fendi Baguette the designer It bag of the early 2000s (which Fendi has recently reissued), and they turned Manolo into a household name. Parker's quirky, high-fashion outfits may not be all that accessible, but she showed people how to express themselves via fashion and that it should ultimately be fun.
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Zendaya
There's no press tour like a Zendaya press tour. With the help of Law Roach, her looks for each are on-theme for the project she's promoting but not in a costumey way. Her looks for Challengers were tennis- (or tennis ball–) inspired; for The Drama, subtly bridal-inspired; and for The Odyssey, they channeled the Greek goddess Athena, whom she portrayed in the film. Method dressing, if you will. Her off-duty style is far more casual, but not without an avant-garde It item here and there.
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Bella Hadid
One day Bella Hadid is wearing a custom Schiaparelli Haute Couture sheer gown on the red carpet at Cannes; the next she's wearing a cowboy hat and low-rise flared jeans, and she looks equally comfortable in both opposite-ends-of-the-spectrum looks. A true supermodel, she's a chameleon on and off the runway. Her outfits regularly include vintage and archival pieces that delight fashion followers.
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Mary-Kate and Ashley Olsen
Mary-Kate and Ashley Olsen haven't taken the most linear of career paths, but in one way or another, they've been shaping our style for years. While we may not get as many sightings of the duo as we used to, their influence is ever present. The Row, with its signature minimalist aesthetic, has become one of the most sought-after brands in the industry, constantly shaping what people wear and what other brands design.
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Beyoncé
There are celebrities, and then there's Beyoncé. No one shuts down a Grammys red carpet like her or elicits as much buzz at the Met Gala. Also known as Queen Bey, she has a regal wardrobe to match her nickname. She's given us countless eras throughout the years, and her most recent, the Cowboy Carter era, can largely be credited for the rise in popularity of all things Western in recent years. It's just one example of her vast influence.
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Zoë Kravitz
Simply put, Zoë Kravitz is the ultimate cool girl. Over the years, her looks have become more minimalist (thanks in part to her go-to brand, The Row) but never without a hint of the edge she's long been known for. For events and the red carpet, she's a Saint Laurent devotee (and a longtime face of the brand) and routinely proves how interesting an all-black outfit can be. It's safe to say that if we get a glimpse of her wedding dress for her eventual nuptials to fiancé Harry Styles, it'll influence bridal looks for years to come.
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Kendall Jenner
Kendall Jenner's face is one you've seen often on Who What Wear over the years, as pretty much every outfit she's photographed in is quickly posted about. Of the influential celebrities on this list, her style is one of the most evolved. In the earlier days of her career, her looks were trendier and bolder than they are today. Fast-forward to post-2020, and she's embraced more of an elegant, luxurious aesthetic, made up of pieces from her go-to brands such as The Row, Toteme, and Khaite.
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Kate Moss
The influence of '90s supermodels continues to have a hold on what we wear, and no one exemplifies that better than Kate Moss. As you may recall, her collaboration with Topshop circa 2007 created a shopping frenzy that went on for many years, and none of us will forget her iconic Calvin Klein ads. Her outfits from decades ago are still as relevant as they were then, and she continues to inspire with her present-day looks, which include a mix of styles from decades past and the trends of today. No one can make a pair of skinny jeans, boots, and a flowy blouse look cooler.
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Nicole Richie
Nicole Richie has been a Who What Wear girl in every way from the day we launched. (Fun fact: She even filmed an episode of her reality show Candidly Nicole at our office.) With her ruffled dresses, denim miniskirts, floppy hats, oversize '70s sunglasses, and low-rise jeans, she deserves much credit for making the boho look a thing. Her current look is more sophisticated and elegant, but it's not without her signature effortless, carefree vibe.
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Harry Styles
Harry Styles may not be completely responsible for making quirky menswear cool, but he's certainly played a significant part. His gender-bending on-stage and red carpet looks have a permanent place in the minds of many of us, and his off-duty outfits, which regularly include handbags, neck scarves, short shorts, workwear jackets, and retro sneakers, have followers of his style thinking outside the box more than ever.
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Kim Kardashian
It goes without saying that Kim Kardashian has had countless memorable style moments over the years. She favors avant-garde pieces and formfitting silhouettes, the latter of which led to the formation of her wildly popular brand, Skims. Aside from that, we'd be remiss not to mention that she famously wore Marilyn Monroe's most iconic dress to the 2022 Met Gala, in a move that's likely to go down in Met Gala history.
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Sienna Miller
Sienna Miller was a boho-style icon in 2006, and she continues to have that distinction in 2026. That said, she has a more polished approach now—one that never feels dated. If Miller wore skinny jeans and Chloé Susanna Boots, we all wanted to wear the same. Her red carpet style since she rose to fame has always been cool, a bit quirky, and never boring. Over the years, she's worn flapper dresses, romantic ruffles, sheer empire-waist silhouettes, crochet, tie-dye, feathers, and sequins, always standing out among a sea of LBDs at any event she's attended.
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