The Decade in Fashion

See ten years of red carpet hits, misses, and unforgettable fashion moments.

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Though Sex and the City kicked off in 1998, the cult of fashion surrounding the show (and, in particular, Carrie Bradshaw) really hit its fever pitch at the beginning of the decade, making brand names like Manolo Blahnik and other six figure footwear lines into household names.
Before Angelina Jolie was a humanitarian ambassador and red carpet favorite, she was a bit unpredictable, style-wise. In 2000, she picked up an Academy Award for her dark, moody turn in Girl, Interrupted, and opted for a seriously witchy look. Influenced by her critics or not, Angelina wore a sexy white suit the next year.
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She may have had talent as an entertainer, but it was arguably this barely-there Versace dress that put Jennifer Lopez on the map. Standing next to her then-boyfriend Diddy at the 2000 Grammy Awards, she was so eye-catching that the world forgot about the gun charges that were plaguing Diddy at the time.
While we applaud Ms. Braxton for managing to pull off such a skin-baring dress in 2001 which managed not to expose private parts or cellulite, we can't understand the impulse to don a dress that makes wearing underwear such a challenge. In the annals of Grammy Award history, this dress is certainly on the losing end.
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Before there was Lady Gaga's Kermit the Frog dress, there was Bjork's infamous swan dress. The singer wore the irreverent frock on the red carpet of the 2001 Academy Awards and has been the butt of many a joke since.
Nothing says "America" like good old denim. Yet somehow (shockingly) Britney Spears and Justin Timberlake's matching ensembles at the American Music Awards in 2001 struck entirely the wrong note.
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As ridiculous as Britney and Justin looked, they were at least on to something. As starlets and socialites alike started incorporating more and more denim into their wardrobes (and red carpet appearances), denim prices skyrocketed to $500 or more per pair, featuring all manner of elaborate distressing, studs, whiskering, and more.
When Halle Berry accepted her Academy Award in 2002, she made history as the first African-American woman to win the award. She also wore a breathtaking Elie Saab dress that managed to perfectly toe the line between scandalous (a sheer top with well-placed floral embroidery) and classic (a long skirt and train that was pure elegance).
The same year Halle Berry nailed her red carpet look, Gwyneth Paltrow stunned fashion critics by wearing a goth-like Alexander McQueen dress with an unflattering, shockingly sheer top. After picking up an Academy Award in 1999 wearing a pink Ralph Lauren gown, Paltrow apparently wanted to try something radically different.
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Sports and hip-hop may have made the tracksuit famous, but it was the ladies of Juicy Couture that took the look mainstream (for better or worse). Madonna wore a Juicy Couture zip-up in 2001 and the label skyrocketed. By 2008, the empire was racking up close to $700 million in sales.
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Christian Audigier, the French designer behind Ed Hardy, has a signature look -- colorful graffiti-inspired tees, jeans, zip-ups, and leather jackets -- that rose to prominence and has become a symbol for everything wrong with streetwear. His unapologetic cheesy styling have only added to his image -- GQ crowned him "Emperor Du Fromage" (The King of Cheese).
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We may never know what inspired actress Lara Flynn Boyle to wear a full-on ballerina outfit -- complete with tutu, ribbon lace-up shoes, and bow-topped bun -- to the Golden Globe Awards in 2003, but the get-up certainly made red carpet history... and not in a good way.
We can all thank Ashton Kutcher for this rather unsavory moment in fashion. As soon as the Punk'd star began wearing all manner of trucker hats -- from vintage to ironic to the iconic John Deere variety -- a nation of lemmings followed.
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In 2004, Serena Williams stepped out on the court of the US Open wearing some decidedly unconventional footwear: black sneaker-boots by Nike. While the "boots" actually consisted of good ol' fashioned sneakers with knee-high covers over them, the world of court fashion was never the same.
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That same year, a similar fashion-meets-sport snafu rocked the 2004 Super Bowl, when a portion of Janet Jackson's ultra-sexy wardrobe didn't make it through her half-time show with Justin Timberlake. Lo, a whole new era of FTC regulations was born and the phrase "wardrobe malfunction" entered the common lexicon.
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This was the decade of the expensive handbag; the lust over $1,000-plus statement-making carryalls made designers rush to enter the market. Starlets and fashionistas scrambled to acquire the "It" bag of the instant, like the Fendi "Spy" bag (left, on Mary-Kate Olsen in 2005) and the Balenciaga "Le Dix" Motorcycle Bag (right, on Lindsay Lohan in TK).
In 2000, Katie Holmes was just hitting her stride as Joey Potter, the lovable tomboy on Dawson's Creek. Through the end of the series in 2003, Holmes had a similarly sweet, young style -- often sporting simple, unstyled hairdos, jeans, and simple tops and dresses.
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By 2005, however, Katie Holmes had met and married one of Hollywood's biggest players, Tom Cruise, and her personal style took a (some might say abrupt) turn for the mature and sexy.
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Joey who? By 2007, Holmes' transformation was complete. There was barely a trace of her former style, as the actress chopped off her hair and started to favor incredibly mature and sophisticated ensembles, as well as a fondness for labels like Armani.
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When the pendulum swung away from hip-hop streetwear in the middle of the decade, it swung hard. Dapper artists like Farnsworth Bentley and Andre 3000 brought bow-ties, plaid, and sweater vests to the world of hip-hop. Welcome, nerd chic.
Once favored by West Coast surfers to keep their feet warm out of the water, UGGs, the shapeless booties, became an overnight sensation in L.A. Within a year, the trend had spread east, and the ensuing backlash against the (let's face it, quite hideous) footwear was equally ferocious.
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There once were the bell-bottom jeans of the '70s and the acid wash jeans of the '80s. Ultra-skinny denim became the pervasive look of this decade, paired with strappy sandals or tucked into tall boots.
When you've got it, flaunt it. At least, that's what Hilary Swank did in 2005 with the incredible figure she'd worked so hard to get for Million Dollar Baby, the movie for which she won the Oscar. Her head-turning backless dress was one of the few red carpet looks that managed to expose a significant amount of flesh while still keeping it classy.
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Made most famous on Balenciaga's Spring 2005 runway, gladiator sandals -- in flats, wedges, and heels -- quickly became the decade's most popular style, worn with everything from jeans to evening gowns, giving the whole look a Grecian goddess spin. (Elle McPherson here in 2006).
When Reese Witherspoon won the Best Actress Oscar for her role as June Carter Cash in Walk the Line, she took a page out of the movie's old school style and wore a stunning, glittering 1955 Christian Dior dress that she found in a store in Paris.
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Who among us hasn't passed someone on the street and thought, "total hipster." The look has become iconic -- from clubs in Williamsburg, NY to park-lined streets in Portland, Or. The wardrobe requisites include slim-fitting plaid shirts, vintage (or just dirty) tees, leather jackets, bangs, and most importantly, skinny jeans. Oh, and don't forget the 'tude to match.
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In one of the most dramatic makeovers of the decade, Rihanna went from a stomach-baring, streetwear-sporting singer to a full-fledged style icon with short, punky tresses and an ever-evolving catalogue of ensembles.
Maybe it was an effort to get an even skinner look than skinny jeans, or maybe it was the next step in comfort after Juicy Couture tracksuits, but whatever the reason, leggings have become such a pervasive trend that Lindsay Lohan even created her own leggings line called 6126.
In 2006, Michelle Williams stepped into the limelight in this vivid yellow Vera Wang gown, which perfectly accentuated her blond hair and red lips. She was still something of an indie darling then, but this look pushed her into the fashion spotlight (she has appeared on the cover of "Vogue").
When Mary-Kate and Ashley Olsen started at New York University in 2004, they were quickly declared style influencers for their signature, more-is-more approach to dressing. Bobo ("bohemian bourgeois") style was coined in 2005 to describe the new trend of piling on oversized, beat-up, mish-mashed luxurious pieces.
By 2009, the twins had used their status as style icons to kickstart a new career in fashion. To date they have launched two fashion lines -- The Row and Elizabeth & James -- as well as a new collaboration with JCPenney on a juniors' line called Olsenboye.
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Rachel Zoe really was a stylist to the stars before she was an "I die"-squealing TV personality. Her influence in the form of high-end long vintage gowns, piled-on accessories and fur jackets was seen on starlets like Nicole Richie and Kate Hudson. Now she's a red carpet fixture herself, preaching her brand of "wear more, not less" style to the masses.
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Amazingly, UGGs weren't the most hideous footwear to become popular this decade. Crocs -- plastic-looking, perforated, outdoor gardening-type shoes that are (we'll admit it) shockingly comfortable -- took the country by storm in a variety of shapes, colors, and iterations, amassing fans like star chef Mario Batali, who prefers his in orange.
Yves Saint Laurent, one of the most influential designers of the century, was one of the first to establish "ready-to-wear" as a respected part of fashion (as opposed to only haute couture), and to take inspiration straight from the street style of Paris. His death in 2008 was attended by supermodels, starlets and political luminaries.
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On election night in 2008, the soon-to-be First Lady chose a black-and-red Narciso Rodriguez dress that struck a sour note with fashion critics. Some even went so far as to call it "hell-colored." You can see more of her looks here.
Singer and famous "Newlywed" Jessica Simpson may have become famous for her hot figure in a pair of Daisy Dukes, but it was the unfortunate high-waisted pair of denim jeans she sported in January of 2009 -- showing off her newly curvaceous silhouette -- that really generated tabloid headlines.
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She became famous for a hit single, but Lady Gaga's eccentric red carpet style has made her an icon. For better or worse the lace face masks, Kermit the Frog outfits, and Alexander McQueen platforms landed her a "Stylemaker Award" from Marc Jacobs at the Annual Accessories Council Excellence Awards in 2009.
Mad Men's launch in 2007 set off a nationwide obsession with slick '60s style -- from skinny suits to swing coats and curve-hugging office dresses.
When Blair Waldorf and Serena van der Woodsen hit the scene in 2008, the fashion set's fascination with collegiate style was reborn. Fans argued who was more stylish -- Blair, with her prim style; or Serena, with her citified bohemian look. The show's stylist, Eric Daman, even published a book entitled You Know You Want It: Style-Inspiration-Confidence.
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From the day she stepped foot in the White House, Michelle Obama has made indie designers like Isabel Toledo and Jason Wu into household names, and re-established the "it" factor of major brands like J. Crew with her trademark mix of mid-price and high-end pieces. We could all take a page from her "style guide".
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