Awards season may still be around the corner, but we've had our eyes on the prize all year. You see, though a grade-A ensemble may seem like less of a production than a film, we know that a blockbuster outfit is truly an achievement. So for this year's best-dressed round-up we wanted to give credit where credit is due and single out the most stellar sartorial performances of 2009. All twelve of these well-dressed winners have played roles in making this year memorable, so we wanted to pay tribute to their particular clothing contributions in our inaugural edition of Who What Wear's Style Awards. So without further delay, the envelopes please…



Readers' Choice
To kick-off this year's awards, we absolutely had to start with the one woman whose outfits constantly demand a standing ovation. After all, we like to think of Who What Wear as chic-ocracy, and when the people (that's you, dear readers) speak, we listen. This was a banner year for In Style's newest contributor, who managed to look amazing whether she was tooling around town (in Miu Miu and Chanel), or hitting the red carpet in polished fare (such as the Brian Reyes frock she wore to a fashion week event in February). Needless to say, Bilson is undoubtedly on the top of this year's list!

Best All-Around
This Inglorious Basterds-stunner certainly had her fair share of exposure this year (her whirlwind promotional tour around the globe made our heads spin!), and yet we never tired of seeing Diane Kruger immaculately turned-out time and time again. True, we devoted ourselves to tracking her stellar promotional looks for the aforementioned film, but we were also quite charmed by her off-duty outfits, too. Though she often opted for Chloe (as seen above for a morning show appearance) or head-to-toe Chanel (le sigh), Kruger was most certainly the best in show!

Most Muse-Worthy
Although there are innumerable titles we could bestow upon Vanessa Traina, we truly think that Most Muse-Worthy sums it up best. You see, many pretty girls can look chic in Givenchy, Proenza Schouler, and Balenciaga (as she does above, wearing a Nicolas Ghesquiere floral frock at the haute couture shows in July), but only a select few can earnestly call themselves true co-collaborators and sources of inspiration. Alexander Wang has admitted to designing with his old friend Traina in mind, and her buddy Joseph Altuzarra (the much-buzzed-about New York up-and -comer) even enlisted this stylist-assistant to walk down his S/S 10 runway.

Most Influential
While we aren't alone in spotlighting this dynamic duo as the most iconic fashion-stars of the decade, we really wanted to give the Sisters Olsen credit for their wildly successful designer doings. This year alone, MK and A have expanded their lines, The Row and Elizabeth and James, into footwear, eyewear, and menswear and were the youngest designers to be inducted to the Counsel of Fashion Designers of America (not to mention they also announced Olsenboye, their collaboration with JCPenney). And because they were able to do all of this while maintaining their signature soigné and off-beat brand of chic, we had to name the Os the all-stars of the 'OOs.

Most Stylish Social
Aspiring actress Byrdie Bell staked her claim as best-dressed social early on this year, and has yet to relinquish it! Though her amazing Brian Atwood over-the-knee boots were her constant companion this year, we like how she never attended any ball or gala this year without also bringing the chic—just see her ravishing reverse-mullet gown (party in the front, business in the back) which she wore to the Museum of National History's annual dance in March, and you'll know what we mean!

Best Import
When Alexa Chung landed on American soil she started a serious sartorial revolution. The former-It's On host's tomboy-meets-It-girl clothing (who else can pull off chic shorts and a button-up and J.Crew leopard belt with such panache?) was as compelling to witness as her witty interview banter. Whether the it-Brit was wearing a vintage leopard coat, her signature striped tees, or just toting her namesake Mulberry handbag, 2009 really served to ramp up Chung-mania!

Best M.O.D. Style
Here at Who What Wear, we had a challenging time pinning down which award Wasson should receive. She's not just a muse, but also a creator (her LuvLow body jewelry line is a smash and RVCA x Wasson line showed at the Bryant Park tents this past fall). But in the end we all agreed that this vintage-loving lady was so emblematic of the MOD-style craze that this mantle had her name all over it!

Best Uptown/Downtown Mix
Though she's known to steal the scenes as the delightfully vicious Blair Waldorf on Gossip Girl, it was Leighton Meester's marvelously dramatic dressing that captured our attention off-screen. We love the way she nails the prim-and-preppy UES look so well for her day job, but then opts to support more directional designers—like Christian Cota and Christopher Kane—for her nighttime events. Whatever style she is sporting, we are more than happy to sit back and watch as this small screen star makes big fashion waves!

Best Fashion Pro
Whether Zoe was rocking a '70s-inspred jumpsuit fit for a Studio 54 dancing queen or a Marc Jacobs obi belt and her signature sky-high heels (as she did to the Stella McCartney-hosted screening of the film Home), we were hard-pressed to find a better dressed fashion professional who is as high-profile and in-demand as the reality-television star. Because this behind-the-scenes chicster looks as OOC on the red carpet as most of her clients do, and was able to provide a snapshot of what it takes to be a heavyweight in the frenetic fashion industry, Zoe is truly deserving of this accolade!

Risk-Taker Extraordinaire
Whether she was early-adopting the strong-shoulder trend in a directional Dolce & Gabanna suit at last year's Met Gala or letting her luxurious side show by wearing a monogrammed hand-warmer to Chanel's S/S 10 barnyard extravaganza, no one imbued the fashion scene with such drama as Rihanna did. We always appreciate when people are willing to push the envelope and make bold statements, so it is no wonder that this songbird stole the show this year!

Most Fashionable Fixture
In a world full of uncertainty, you can always depend on one thing: Olivia Palermo will look polished and put-together whenever she leaves the house. Although it seemed that the ELLE editor-in-training was incapable of making a mistake this year, we really wanted to applaud Palermo for her consistently cute and delightful ensembles and her determination to distinguish herself as a fashionable fixture with stylish staying power!

Future Icon
Though Jagger was just awarded with the British Counsel of Fashion's award for most promising newcomer, we at Who What Wear have steadily been tracking this rock star daughter-turned-model for quite some time. Though she presently looks quite stunning in her glamour-puss ensembles (like the va-va-voom Vivienne Westwood frock that she wore to the UK premiere of Where the Wild Things Are) and has traffic stopping good looks (she shows off her impeccable genes in the Hudson jeans campaign), we really think that the sky is the limit for this icon-in-the-making!