2009 Emmys Fashion Winners

Peaches and Gleam: For several frustrating months now, Drew Barrymore has been exploring fashion's final kitschy frontier, styling everything from tie-dyed leggings accented with a shark hat to plaid thigh highs accented with plaid, plaid and more plaid. And let's not forget her recent experimentation into black-tipped tresses, which she took to the next kooky level by slipping on an outré dress that complemented her two-toned coif. But the sunny star goes from eccentric to ethereal at the Emmys in a peach blush Monique Lhuillier confection and a sophisticated swept-back 'do that keeps her inky, icky ends tucked away. Sure, the bodice could fit a mite more snugly, and the neckline could use a bit of sparkle, but the softness and sweetness radiating from Drew is undeniable. And it's a welcome change from her long line of wackadoodle (but, hey, adorably so) fashion statements.
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Swell-egant: Heidi Klum's red-carpet stroll may have prompted panicked bystanders to boil water and time her contractions, but it also led to plenty of oohs and aahs over her ability to look ridiculously gorgeous while hauling around what amounts to an about-to-pop beach ball. The "Project Runway" mogul's beaded and lace-trained Marchesa gown is designed to highlight, not hide, her Jiffy-popping belly. And while the silhouette might cling too tightly for some stork-awaiting stars, the soon-to-be mother of four has the confidence necessary to make it work. Heidi finishes off her bountiful couture with a few timeless accoutrements: a pair of cascading diamond earrings (each lobe is weighed down with 90 carats, in case you were wondering) and her skinny-tied, perpetually debonair hubby, Seal.

Red, White and Whew: We spent ages mulling over whether "Gossip Girl" stars Blake Lively and Leighton Meester belonged on the best- or worst-dressed list. An argument can be made either way, so how 'bout we run through the pros and cons? Pro: With Blake's nubile body and her fabric-taping skills, she's naughtily showstopping in this navel-plunging red dress with a sexy slit that gives a clear view to her thigh's upper east side. Con: We're very uncomfortable seeing this much of Serena's perky van der Woodsens. Pro: Leighton earns haute couture cred by once again nixing the safe, Blair Waldorf-ish route. Con: A goddess gown requires more styling than simply tying knots in Zeus' bedsheets. Pro: Blake's minimal makeup and pulled-back mane highlight her gorgeous bone structure. Con: The tapered, rigid braid she's sporting worked better on a tomb-raiding Angelina Jolie. Pro: Leighton's apple cheeks, snow-white complexion and ruby red lips will inspire lifelong devotion from seven vertically challenged men. Con: Puff pastries, while delicious, do not belong on one's shoulders. Pro: Unlike most of their fellow actresses, Blake and Leighton took a chance, and for that they earn a onetime get-out-of-fashion-jail-free card.

Power Tulle: The Emmy red carpet is packed to the gills with the same silhouettes, including enough fishtails to make a mermaid cry for mercy. But Mila Kunis offers a refreshing alternative with a maroon Monique Lhuillier tulle gown that hits right at her ankle. Equal parts modern and retro, girlish and Goth, this airy layered ballerina frock could easily take the teeny actress from a garden party tossed by Audrey Hepburn's couture-bedecked Sabrina to a night of club-hopping with her longtime squeeze, Macaulay Culkin. And while we wish Mila had opted for a shoe that didn't come from Mickey Mouse's new platform collection, her vintage chandelier earrings and dramatic eyes happily keep our gaze high above clodhopper level.

Gold Standard: Sandra Oh gets everything right in a strapless, gold-bead-encrusted Marchesa column. It's probably the most fabulous red-carpet look the "Grey's Anatomy" actress has ever put together. And she earns top marks for the gown's second-skin shape, which emphasizes her enviably weensy waistline, and for her soft, blown-out waves and bubblegum-hued Jimmy Choo heels. And even though we have an overwhelming urge to tug on Sandra's tassel belt in hopes that the hemline hoists up, Broadway curtain style, the temptation does nothing to tarnish the shine on this sublime ensemble.

Peeping Up With the Jones: January Jones ditches her demure "Mad Men" A-lines and shimmies into a fashion-forward architectural creation from Versace. The gathered, floor-sweeping skirt has the faintest hint of mint, while the deco-inspired, peekaboo cutout, glass-beaded bustier gives off a whiff of girl power by borrowing heavily from the design of Wonder Woman's eagle-emblazoned breastplate. The only thing missing: matching bullet-deflecting bracelets.

That Curtain Something: Draping is a delicate science. Just a smidge too much, and you could end up looking like a sophisticated window treatment. But Kate Walsh gets the curtainy balance right in a strapless, sweetheart-necklined J. Mendel gown in a crystal blue hue that plays off her lightly bronzed skin. The folds hanging from the "Private Practice" star's hips might have overwhelmed her figure if they'd had any extra oomph, but the dainty droop (the first and probably last time we'll ever use that phrase) brings the feminine lines into focus. And while the frock's frosty tint is well-suited to Kate's coppery 'do, the coif itself is too casual, the result of letting armchair stylists (meaning us schmos at home) choose her mane arrangement in a Suave-sponsored poll.

Byrne After Beading: Rose Byrne figures out a stylish way to maintain her personal space on the red carpet by climbing into a gown with a built-in tulle security perimeter. The "Damages" actress successfully supersizes in this crystal-beaded, fairy princess-poufy Valentino. But she keeps the rest of her look neutral, opting for barely there makeup and an everyday (as in, this is our hairstyle, every single day) bob.

Messing in Action: Debra Messing does her best to make the studio suits regret their decision to cancel "The Starter Wife" as she breezes into the Emmys looking flawless in a crimson, one-shouldered Michael Kors column. Between the carpet and the actress's sideswept auburn mane, it's a whole lotta red. But she keeps from blending into the background with some glittery help from the oodles of Swarovski crystals twinkling on her gown, as well as gold earrings and matching cuff bracelets that likely prompted her stylist, Rachel Zoe, to sigh, "I die."

Once in a Blue Swoon: We've never actually caught an episode of "The New Adventures of Old Christine," but if Julia Louis-Dreyfus' sitcom is half as good as her subtly pleated Vera Wang frock, then we're gonna give it a try. The actress is simple, classic and unfussily lovely in this draped, deep teal number with a crisscross strapless bodice and black belt. She keeps the accessories to a minimum, wisely letting her soft curls, lobe-extending diamond-drop earrings and winsome visage, which has remained virtually unchanged from the days when she was yada-yada-yada-ing on "Seinfeld," take center stage.
Check out the 2009 Emmys Fashion Losers
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