Um, No: The Best of the Worst of 2009

Since we've been covering the style set's (often egregious) fashion missteps, there's been bad -- Mischa Barton's "Spiderwoman" dress -- and then worse -- Leigh Lezark's carnival clown suit. Here are our top 20 most memorable fashion flubs.

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2/21
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Gossip Girl Leighton Meester went for a rock 'n' roll look at the grand opening of American Eagle Outfitters (where she also performed). Unfortunately, she went a little overboard. We can see how each of the elements involved do seem very "rock star": the heavy eye makeup, the leathery dress, the bared skin. However, all of these elements in conjuction just make a girl look straight-up crazy.
3/21
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There are no words. Amber, we're sure you think your body is bangin' (and, to be fair, it kind of is), but for the love of all that's holy, we're tired of looking at it. The only thing at the VMAs worse than Kanye's drunk-guy-in-a-bar behavior at the show was Ms. Rose's ridiculous-looking python bodysuit. Maybe it's time for both of you to lay low for a while.
4/21
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Always taking style to the next level, socialite Tinsley Mortimer took the alarming trend of frothy, flowery embellishments and added some extra tiers at the grand opening of the City Opera. The result, alas, is more cake than fashion. We haven't seen ruffled layers like this since our aunt's '70s wedding.
5/21
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Okay, we get it. Sienna Miller has incredible legs. But considering this is her big Broadway debut and all, we were hoping she'd go for something a little more sophisticated. Or at least a dress that didn't look like it had been clawed by a wild animal.
6/21
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Granted, she's got a hot body, but that's no excuse for the skimpy spectacle Bai Ling flaunted on the benefit circuit. Unless her stylist is a seven-year-old girl with a skater boy crush, unlimited access to Jon Gosselin's wardrobe and has grown up in a naked house, we can't think of the motivation behind this outfit.
7/21
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It should be said, first of all, that Ivana Trump is a dame in the truest sense of the word, and most of the time we're in favor of her all-out glamorous style. In this instance, however, Ms. Trump probably should have steered clear of a strapless mini. We respect her no-holds-barred red carpet approach -- age-ists be darned! -- but on the other hand, we might recommended a crisp jacket or shawl, or a dress that was less ... Bright? Shiny? Just less. Or more. You know what we mean.
8/21
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We were all ready to celebrate Mischa Barton's triumphant return after her scary stint in a psych ward ... until she showed up wearing this. At this point, wouldn't you be trying to re-establish your credibility in the industry by wearing something chic and ladylike -- maybe a little bit French? Now is not the time to arrive at an event wearing a sexy spiderwoman get-up and romp around a party with Heatherette's Richie Rich.
9/21
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For those who, like us, feel there's been a cult developing around the alien-like, towering heels from Alexander McQueen's Spring 2010 collection, Ms. Daphne Guinness officially became the first live red carpet specimen to wear them. The reigning trend has been to go whole-hog with these -- exhibit A: Lady Gaga, and now exhibit B: Ms. Guinness, whose adventurous styling puts her a bit closer to Bride of Frankenstein territory.
10/21
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Blake Lively attended the after party for "The Private Lives of Pippa Lee" at the Ace Hotel, wearing an incredibly low-cut white jacket and what appears to be either the shortest miniskirt we've ever seen or biker shorts. As things stand, Ms. Lively is getting into a troubling trend of wearing low-cut tops and short skirts, which is a pretty well-established "no-no" in most fashion circles, even for someone as well-endowed as she is. In this case, the expanse of flesh exposed seems all the stranger considering the slightly old lady-ish vibe of the bow-clasped embroidered blazer. Granted, it does have a perfectly-tailored French couture feel, but stand down on the flesh exposure, already.
11/21
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Remember how we said Emmy Rossum really never falters when it comes to red carpet events? Well, maybe she got tired of being "the good one," and decided to try a headache-inducing bodycon dress by Ferragamo at GQ's Gentlemen's Ball. Hey, even Gwyneth went goth that one time, and we know she bounced back.
12/21
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Okay, Juliette Lewis, we get it. You're a big, awesome, eardrum-busting rock star. Your band opened for the Pretenders last night! You don't have to prove it to us by attempting a death-defying combination of polka dots, sequins, chiffon, and ribbons. For Pete's sake, it's still daylight in this photo. In our humble opinion, this is the kind of ensemble that can only come out after midnight.
13/21
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We're not sure who advised young Ms. Olivia Thirlby that a hot pink ruffle-front shirt, paired with what appears to be a silver tuxedo, would be a good idea to wear to a fashion show. Eye-catching, for certain, but not necessarily a good idea. For one, the entire ensemble has the costume-like effect of a bad '70s rental tuxedo -- the kind of thing the guys in Dumb & Dumber might want to wear. But even worse -- and much more concerning -- the whole outfit doesn't exactly flatter Ms. Thirlby, who we know to be a lovely girl and quite well-proportioned.
14/21
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Full disclosure: We, too, have dreamed of dressing up like a Vegas showgirl and serenading a crowd. But if we actually, like, booked the Today show (as Katy Perry did), there's no way we'd actually do it. As is, this is somewhere between over-the-top Vegas and a skeevy New York taxi cab. Stellar hair and makeup, though!
15/21
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We appreciate that "Ugly Betty" star Becki Newton was likely going for a high fashion look when wore Prabal Gurung to a The New York Times panel, but she ended up looking more like a bird puffing up in an elaborate mating ritual. She's a very petite girl, and the explosion of white ruffles on her chest is just overpowering, especially considering that it fades to skin-baring mesh at the back -- couldn't they have spread that material out a bit?
16/21
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New York DJ and model Leigh Lezark rocked a series of edgy, on-trend looks throughout her New York Fashion Week run (we even forgave her a certain see-through ensemble because, hey, the runways seemed to be packed with underwear), but she seemed to have missed a step in Paris, ending up in a modern art-inspired clown suit at Chanel's Spring/Summer 2010 show. the more we stare at it, the more it looks like a circus performer's leotard, complete with star-shaped pasties.
17/21
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Lily Cole takes an acting turn in "The Imaginarium of Doctor Parnassus," which is always a big step for a model. Unfortunately, she decided to celebrate by wearing pinstripe hot pants. Granted, there's a certain matchy-matchy appeal to the ensemble in an "oh look, the pinstripe jacket and shorts match the thigh high boots" way, but then again ... the boots are ALSO pinstripe? Oh dear.
18/21
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Okay, you two. You're both handsome men. This has to be stopped. Lorenzo Martone: You're wearing nerd glasses and suspenders. Now, were those two things to be separated, maybe we could make this work. As it stands, this looks like a costume. Or a tribute to Steve Urkel. Marc Jacobs: You're wearing a skirt and carrying a clutch. We're fans of both, but again, by combining the two you seem to be pushing the envelope.
19/21
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It's no secret that Gossip Girl's Taylor Momsen has developed a penchant for wearing rather scandalous attire and entirely too much eyeliner. This ensemble, however, takes it to a new level. To top it off, if there's one thing that will emphasize pantslessness even more than, well, not wearing pants, it's black thigh high stockings and a garter.
20/21
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Just when we were thinking the wild fashion set had fled abroad of late, here comes Lady Gaga in an outfit that seems to made entirely of the ruffled trimming off a grandmother's bedskirts, topped off with Alexander Wang sunglasses, which -- we should point out -- aren't even available to buy yet. We understand Gaga's on-stage outfits and even relish her over-the-top head-to-toe lace craziness, but this just looks like granny lace and granny panties.
21/21
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Ashanti turned up to celebrate the 70th anniversary of "The Wizard of Oz" in a not un-flattering strapless dress and a pretty charming bouffant hairstyle. However, honey, there is no place for that color pink in the morning light of day, especially in a chilly New York September. We might have suggested something a bit less spring pastel-y -- perhaps ruby for Dorothy's slippers?
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