Fashionista 25 Trendsetting Celebrities

In Hollywood, Scientologists and Kabbalists alike worship the same God – the almighty lord of fashion. In a town where Versace and Armani retain deity status, it’s pretty much a career deal-breaker to not follow the style laws set forth by the more innovative stars that set the bar of fashion very high. Here are 25 celebrities known for their ability to make and break trends.


  1. Madonna: Definitely the oldest celebrity on this list, Madonna is still setting trends even in her 50s. Madge has been gracing the pages of fashion magazines since she first hit the scene in a pair of fingerless, lace gloves back in the 1980s. The Material Girl made layering, hair bows, and leggings cool over 25 years ago, and she had teenage girls from L.A. to Scranton mocking her style. In the 1990s, she got a little chicer, and, in some respects, much more risqué, before adopting a gothy, hippy look for her Rays of Light era. Madonna’s proving that she’s still got what it takes – for her Confessions tour in 2006, she sported a coveted purple leotard from Dolce and Gabanna that turned the heads of every major fashion editor.
  2. Sarah Jessica Parker: Sarah Jessica Parker was basically hand-delivered her role as one of the most fashionable celebrities on the planet when she nabbed the role of Carrie on “Sex and the City”. While her on-screen character sported ever-more-enviable outfits week after week, Parker seemed to almost be competing with her fictional self in real life. The New Yorker was constantly photographed walking around her trendy downtown neighborhood in even trendier outfits. During the filming of the “Sex and the City” movie last year, Parker’s on-screen costumes made the tabloids and the pages of Vogue. From Christian Dior to the man she made uber-famous, Manolo Blahnik, Parker is trendsetter that will go down in history. She now, predictably, even has her own line of affordable clothes called Bitten.
  3. Katie Holmes: Katie Holmes is perhaps both the most surprising and relevant celebrity to make this list. Less than a decade ago, she mostly graced the “who cares what she’s wearing” pages, as she was usually spotted out and about wearing a ponytail, a bulky Abercrombie sweater and a pair of corduroys. But today Holmes, the wife of megastar Tom Cruise, can more commonly be seen in Armani, Lagerfeld, and Chanel. Her swan-like transformation must have surely involved the hand of a high-paid stylist, but the pricey price tag on that service was well worth it. Holmes may not have look-a-like, copy cats following her around, but her sleek and classy style is definitely worth copying and certainly worth noticing.
  4. Victoria Beckham: Famous for being one-fifth of the UK pop group The Spice Girls, Beckham’s fame survived the group’s disbanding when she married soccer hottie David Beckham. With her music career in the dumps, Posh Spice had some free time on her hands. So she turned to fashion and hasn’t looked back since. Beckham is well-known to always be wearing the latest and greatest items from the highest-end designers and she has even started a few trends of her own – remember her angular, bob haircut? She sent stylists across the country back to training so they could recreate the look on every plain Jane who started demanding it. In addition to inspiring trends, Posh Spice has also done some designing of her own – a denim line for Rock & Republic called “VB Rocks” and in 2006 a line of jeans and sunglasses called dvb. She has also landed quite a few spokeswoman contracts, and has even worked as a stylist on many photo shoots.
  5. Nicole Richie: When Richie began dropping weight like crazy following the first season of “The Simple Life”, it seemed like every pound lost was chronicled in the press. But with her new waif figure came a more concentrated approach to her style, and while the tabloids criticized her figure with one hand, they praised her fashion know-how with the other. Richie is known as one of the best-dressed stars in Hollywood today, and there’s even a blog that chronicles her outfits every day! Whether she’s cleaned up in a sleek Missoni dress or dressed down in a flowy shirt and ripped jeans, Richie always looks spot-on cute.
  6. Gwyneth Paltrow: Paltrow is a girl that designers love to dress – especially her good friend Stella McCartney, who recently made her a stand out one-piece jumpsuit that got the actress lots of ink while she was out promoting her new film Iron Man. Paltrow has even been tapped to be the face of Estee Lauder, a high honor for a non-model. But ever since she first became famous, Paltrow’s tasteful, simple style has been praised and lauded in the press. A reporter at even congratulated her for being the “classiest label slut,” always wearing the right designer at the right time – Calvin Klein in 1995; Gucci in 1996. Today, Gwyneth gets photographed more for being out with her kids, but, typically, the photo captions will also reference her well-chosen outfit.
  7. Mary Kate Olsen: This tiny actress made a name for herself in the fashion world by taking all the latest trends and wearing them at the same time. Mumu, floor-length scarf, floppy hat, gigantic sunglasses – why not? But though Olsen took loads of hits from the press for her bag-lady style, she also seemed to be sparking something in trendsville. Not long after she began tromping around in her combat boots and layered shirts, lots of starlets starting adopting a more frumpy approach, wearing tunic shirts, scarves, hats, and leggings out shopping or to the park. While Olsen gets to keep the prize for the most overzealous frumpy dresser, she did succeed in inspiring others to layer like crazy. Oh, and accessorize! Don’t forget her rule of thumb: always, always carry a Venti Starbucks in your hand.
  8. Paris Hilton: Hilton’s style is not really that exciting. Yes, she’s always sort of well-dressed, in the sense that her outfits are cute and cost an arm and a leg, but really there’s never anything super notable about her attire. That was until she got a little dog named Tinkerbell. One thing Hilton can certainly get credit for is reinvigorating the “pets as fashion accessories” movement. While it’s true that many starlets from old Hollywood used to do this very thing, it seemed to have completely got out of style in the past few decades. But Hilton resurrected it, even inspiring Britney Spears to run out and get her very own arm-Chihuahua. Lately though, Hilton seems to have swapped out her canine friend for herself, as many recent paparazzos have snapped the socialite sporting T-shirts with her own face and name on them. Narcissism at its finest.
  9. Gwen Stefani: No matter how bold or how crazy, one can’t help but love Gwen Stefani’s rockin’ sense of style. When she started out as the front woman for No Doubt, boys and girls alike drooled over Stefani’s cool, tomboyish look that was always made more feminine by the fact that her abs were exposed and she wore colorful hair accessories and make-up. Pairing plaid work pants and a chain wallet with a bikini top, Stefani looked both sexy and approachable, inspiring a cadre of young teenage girls who didn’t fit the Britney Spears mold to follow Stefani’s lead. Now, Stefani’s style has definitely evolved into something a little more classy, but still funky, creative, and one of a kind. In 2004, she launched her own fashion line L.A.M.B.
  10. Rachel Bilson: Bilson is best known as Summer from the former hit series “The O.C.,” but while her acting career hasn’t given her anything more notable to put on her resume, her personal style has won her tons of fans. The tiny actress is always put together in the latest styles, making trend setting look totally effortless. One blogger, who writes a weekly tribute to Bilson’s outfits, wrote this recently, “Seriously. Her outfits are just always great and this is just how she dresses when she is running errands.” In fact, there are several blogs dedicated solely to the task of monitoring what Bilson is wearing. It’s safe to say that one of her biggest charms is the fact that Bilson makes fashion seem doable to the rest of the world. Her not-over-the-top style makes average, non-Hollywood girls think, “That’s something I could pull together, too.”
  11. Kat Von D: It’s hard to tell how quickly Kat Von D’s covered-in-tattoos look is catching on with the general public, but this ink artist has definitely opened a whole new door in the fashion world for women who aren’t interested in having too much natural skin showing. Von D, star of the new reality show L.A. Ink, owns her own tattoo parlor in L.A. and sports tattoos all over her body. She’s also a fan of tight jeans and cleavage-revealing vests. She’s made rocker girl look both real and cool and has given tattoos a place in women’s fashion.
  12. Jennifer Lopez: J. Lo has not only brought big booties back from the dead of the curve-loving 1950s, but she has also managed to make hip-hop street style (as well as Miami-inspired floral prints and cut-out dresses) classy and glamorous. Remember her floppy hat and lace-up pants from the “Jenny from the Block” era? Who could have thought that an outfit normally reserved for a prostitute from 1975 could look so stylish? But then she turns it around and starts making plunging necklines the thing to do. Who could possibly forget the outfit she wore to the Grammy Awards in 2000, with its neckline nose-diving well below the naval and its see-through skirt? That dress is surely one for the history books.
  13. Amy Winehouse: While we hate to call a crack addict and alcoholic a trend setter, we have to admit that Winehouse’s look is certainly a signature one. Who else could sport a beehive, dramatic, thick eyeliner, tattoos, and miniskirts and look great? Well, great if you don’t count the crazy-eyes and cut marks. Winehouse’s musical and personal style are definitely one of a kind and they’ll stay that way. Anyone who even tried to copy her would quickly fall to wanna-be status.
  14. Missy Elliott: Big, ornate hoop earrings, head-to-toe matching outfits, messenger caps, and flamboyant sneakers – that’s the style of hip hop artist Missy Elliott in a nutshell. She’s the woman who made the old school track suit both stylish and feminine. Wo said only guys can wear tricked out Nikes? Elliott is also a trendsetter in her music videos. Remember the trash-bag-looking thing she wore in her “Supa Dupa Fly” video? While Elliott’s copycats most certainly come from a different sort of sub-culture than those emulating Rachel Bilson, she can be given partial credit for at least one mainstream trend – the sideways pageboy cap. Heck, even Paris Hilton kicks those these days!
  15. Chloe Sevigny: On her TV show “Big Love,” Chloe Sevigny plays a polygamist Mormon and her costumes consist of floor-length denim skirts and turtleneck prairie shirts. But in real life, Sevigny is a fashionista of the highest caliber. She’s the girl hipsters fawn over with her heroin-chic figure and her adventurous way of dressing. She’s been known, on separate occasions, to rock only a sweater with ankle boots or a tiny leotard dress that looks like it was meant for the Ice Capades. Sevigny usually sticks close to the hipster designers of NYC, like Marc Jacobs and Zac Posen, but overall she has a pretty wide palette and is definitely worthy of style icon status.
  16. Jay-Z: Jumping genders for a minute, let’s talk about Jay-Z. The so-called “best rapper on Earth” is also known to be quite the style setter in hip-hop fashion. Jay-Z himself always looks classy and in charge, whether he’s wearing a suit or a basketball jersey. And he’s taken his love for fashion a little further than simply being a model for other people’s clothes. He co-founded the label Roca Wear, which sells over $400 million each year in merchandise. Jay-Z also designed a line of Reeboks that made him a cool $100 million. The man clearly knows clothes and business.
  17. Joel and Benji Madden: These brothers, who head up the band Good Charlotte, have had their own signature styles ever since they came on the scene in 1996. With Benji’s trademark fedora cap, which he is rarely seen without, and Joel’s mini-mohawk, both brothers are always decorated from head to toe in tattoos, diamond earrings, sunglasses, and loud, vintage T-shirts. So recently, they decided to parlay their personal styles into a little extra moolah. They launched their own clothing line DCMA in 2006, which used to be called MADE clothing. Originally just a T-shirt line, DCMA now makes hats, belts, baby clothes, hoodies, and soon will release a line of sneakers. Because the brothers just opened their first retail outlet in L.A., the line has been garnering lots of attention from both the press and other celebrities who are helping the Maddens promote the line by wearing the products all over Hollywood.
  18. Travis Barker: Before the Madden brothers, however, there was Travis Barker, former drummer for Blink 182, who almost single-handedly brought the Mohawk back into style. In addition to setting a new hair trend, the tattooed and pierced drummer also has his own line of skateboard apparel called Famous Stars and Straps. Barker started the line in 1999 when he began making T-shirts for his friends and band mates. Those designs generated interest from outside parties and so he expanded his hobby into a business that now makes shirts, sneakers, and skateboard gear.
  19. Kimora Lee Simmons: The ex-model and ex-wife of Russell Simmons latched onto the coattails of her ex-husband and rode them high. During their marriage, Russell Simmons launched the ubiquitous hip hop clothing line Phat Farm. Kimora Lee launched a side line off of that venture for women called Baby Phat, which specializes in booty-licious clothing for the hip hop girl looking to add a little sex appeal and bling to her wardrobe. Think huge, gaudy handbags, loud sneakers, six-inch heels, and blinging belts and earrings. It’s doubtful that you would catch the Chloe Sevignys of the world decked out in Baby Phat gear, but Kimora Lee has managed to become a style icon in her own right amongst many women with a little junk in their trunks.
  20. Fergie: The female component of the Black Eyed Peas recently launched a successful solo music career, but she has been getting kudos from magazine editors and fans alike for more than her musical chops. Fergie’s fashion-forward style leans more toward short shorts, sleek pantsuits, high heels, and any outfit that shows off her chiseled abs. She makes hip hop style feminine and demure by pairing baggy bottoms with tight, cropped tops. And she’s not afraid to show off her physique, often wearing short, short, tight dresses. Fergie makes her style her own by combining elements from many different genres.
  21. Lauren Conrad: While it’s easy to argue that Laruen Conrad, of “The Hills” and “Laguna Beach” fame, doesn’t really deserve any street cred for her pseudo-famous status, she is getting more and more press for her efforts as a fashion designer rather than her non-efforts at being a reality TV star. Her brand, Lauren Conrad Design, is pretty staid and not at all exciting, but then again it’s the sort of stuff you see just about everybody wearing these days. Did she copy the masses or did the masses copy her? Hard to tell, but we think that among the high school contingent of gossipy girls who hang on every word Lauren Conrad mutters on “The Hills,” she probably holds some sway. At this point, though, it’s doubtful Vogue will come calling anytime soon.
  22. Mischa Barton: This other former star of “The O.C.” may not be quite as iconic as her buddy Rachel Bilson, but Mischa Barton is definitely a favorite of the photogs for always rocking high fashion on the streets of L.A. Tapped to be the face of Bebe, Barton’s tall figure has gotten her more modeling contracts than petite Bilson can ever hope to see, but Barton’s personal style is much less skimpy Bebe and much more 1960s hippy. She digs leather, high-waisted pants, suede moccasin boots, and head scarves. Her free love fashion has definitely earned her some fans – there’s a few websites dedicated to tracking her daily styles, as well.
  23. Agyness Deyn: This British model may not be known to too many folks in the regular world, but when it comes to fashion she makes big waves of which bloggers, reporters and designers alike are taking notice. Her pixie haircut and popularity with European designers has earned her the nickname “the new Kate Mosss.” And when she’s not posing for the cover of Vogue or singing with her band, she’s being photographed walking down the street in shredded jeans or loud layers of scarves, T-shirts, and hats.
  24. Cameron Diaz: Spunky, sporty Cameron Diaz has a pretty moderate, yet tasteful, style day-to-day, but the actress really makes a big fashion splash when she’s out attending events. Consistently named on all the media’s “best dressed” lists, Diaz recently made headlines when she paired a fuchsia floor-length Dior gown with turquoise Fred Leighton jewels. In 2007, she was named best dressed at the Oscars when she wore a white, off-the-shoulder Valentino gown and $2.9 million worth of Cartier jewelry.
  25. Natalie Portman: Natalie Portman is not often spotted at Fashion Week events, but she is seen as a style icon in her own right. This socially-conscious star is known for her red carpet pizzazz, wearing timeless, classic designs with a dramatic flare. Ruffles, lace, stripes and anything by Lanvin are her friends, as are non-leather accessories. In fact, Portman recently launched her own line of vegan footwear called Te Casan.

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