Cheryl Shops

Best & Worst Dressed at the Met 2009 Costume Institute Gala Ball
The thing about the Costume Institute ball is that, this being arguably the biggest fashion-industry event of the year (except for maybe the CFDA awards), there are always models there, and the models almost always look better than everyone else in attendance. (Of course, that's what they're paid to do.) This year's theme being "The Model as Muse," there were even more models there than usual, and, refreshingly, some of them made some rather questionable fashion choices, including several crotch-flashingly high dresses. (See, they don't look good in everything!) So, without further ado...

Best
Liv Tyler, Kate Hudson, and especially Kate Bosworth all look so lovely in Stella McCartney, I am not even commenting on what the designer herself is wearing. And that's saying something.


Ashley Olsen is truly the best advertisement for her own label, The Row. This dress makes me forget that I have boobs too big to pull something like this off.


Jessica Stam could make a garbage bag look hot (and she is paid accordingly), but year after year, she is one of the best-dressed people at this event. And now she's making me want to wear Rodarte.


The models love Rag & Bone, and from Maryna Linchuk's sexy colorblocked minidress to Lake Bell's even-sexier tuxedo, you can see why.


Of all the blast-from-the-past models that showed up at this event, I think I was most excited to see Cheryl Tiegs. Bonus: She looks freaking amazing.


Honorable Mention
I am definitely in the minority here, but I actually like Madonna's outfit, especially the to-die-for thigh-high leather boots. But, then again, if she hadn't worn the Donnie Darko rabbit ears, would we be talking about it as much?


As you all know, co-chair Kate Moss can do no wrong in my book. However, if I had to change one tiny thing about her outfit, it would be the turban. Was it really necessary?


I love Rachel Bilson's Bally dress; her Angelina Jolie hair, not so much. Thankfully, the dress wins.


Erin O'Connor's Gaultier dress is not for everyone, and, yes, she looks a bit Goth in it, but if anyone can lead the '90s minimalism revival, she can.


My first thought upon seeing Claudia Schiffer's Versace gown was, wtf? My second thought was, hmm. My third was, what a gorgeous dress--a thought that might've been influenced by the sheer smokin'-ness of the wearer.


Dishonorable Mention
I love Lara Stone, and I love Alexander Wang, but I do not love Lara Stone in this Alexander Wang dress, which is ill-fitting and slit up to the hoo-ha.


I actually think Agyness Deyn's Burberry dress is quite lovely, and I think it's awesome that she came with Twiggy, but, I'm sorry, I just cannot get past the hair and makeup--it's like the illegitimate child of Barbara Bush (sr.) and Edie Sedgwick.


Oh, Jessica Alba, why did you wear this lovely Jason Wu frock with black opaque tights and chunky black platform shoes--in May?


Anne Hathaway is wearing Marc Jacobs, a designer who readily admits he doesn't do red carpet well. This dress--which makes the otherwise skinny actress look incredibly hippy--is proof. Also, why the Jacqueline Susann hair?


Daria Werbowy is one of my favorite models (MW will bemusedly tell you how I drunkenly shouted "Look, it's Daria!" every time I saw one of her H&M billboards in the Prague subway last year), but, I'm sorry, her Balmain dress is just too damn short.


Worst
Leighton Meester's Vuitton dress wouldn't have been so bad if she had just worn it with bare legs, but, whew! Those Liberace-meets-gymnast leggings are just killing me.


Can someone tell me why Emmy Rossum keeps showing up at these things, especially when she's wearing snoozers like this Carolina Herrera, which looks about 25 years too old for her?


The nicest thing I can say about Jessica Biel's Versace dress is that at least she looks like an expensive French can-can dancer/kept woman.


I can't decide whether I'd like Helena Christensen's Zac Posen dress any better if the uber-cheesy sequined "Vogue" lettering weren't there. I'm going to go with a smidge, but not much.


Blake Lively is quoted in this month's Allure as saying that she feels like a tranny a lot of the time. With dresses like this, I can see why.


Photos from style.com and wwd.com