Oh, Leighton Meester. You made me work hard for this one. Scrolling through endless pages of red carpet events, trying to find five fabulous looks to feature, it was as though Meester spent a good portion of her earlier Gossip Girl days dressing the exact opposite of Blair Waldorf so people would be clear that she was not Queen B on her days off. Well, Leighton, I’m convinced! This would’ve been a whole lot easier if we were just showcasing Blair’s best…but here are five looks from Leighton Meester that I absolutely love (for part 1 with Megan’s picks, click here).
2008 Teen Choice Awards in Lanvin

Image from redcarpet-fashionawards.com
I love this fresh-faced and understated Leighton! This dress makes a strong case for Kelly green being the only colour that olive skinned brunettes ever wear; the shade is stunning on Meester, and the draping is perfectly executed. I even love the skinny belt which gives a flattering fit at the waist. Paired with classic black peep toed pumps, Meester looks like a young woman ready to take on Hollywood!
2009 MTV Movie Awards in Emilio de la Morena

Image from pinky.gr
Here’s the anti-Blair sort of look I was referring to, but in this case I don’t hate it! Meester has an “edgy” red carpet uniform of sorts, consisting of a questionable mini-dress anchored with some sort of heavy looking shoe. That recipe can quickly bake up a dozen hot mess cupcakes, but for this occasion it somehow turned out as perfection pie! Uhh…I guess I have baking on the brain…? Anyway…her face looks flawless, her body looks amazing, and the purple suede booties are fun and young. I am loving it.
The Roommate premiere, 2011, in Michael Kors
Image from ishoppinglifestyle.com
We’ve got the cut-outs again in this look, but it’s a much more classy take on things with this floor length Michael Kors. Considering she’s at a premiere for a movie in which she plays some sort of psycho roommate predator, I think this is a perfect choice, don’t you? She’s got a sort of dangerous/sexy thing going on with the black leather and pin straight center parted hair. Hotness!
2011 Golden Globe Awards in Burberry Prorsum

Image from justjared.com
Okay, first things first…that shoe!!! I want it! It is somehow able to simultaneously stand out and steal the spotlight while blending in perfectly to compliment the romantic long-sleeved gown. Meester avoids any schoolmarm comparisons by rocking a scandalous slit, and wins my heart with this atypical red carpet choice.
Christian Dior Spring 2012 Presentation in Christian Dior
Image from redcarpet-fashionawards.com
I suppose this isn’t technically a red carpet event…more of a cobblestone sidewalk, actually…but it’s at Paris Fashion Week, so I deemed it acceptable! This is some sort of dream look for me, from the ruffles to the tiered skirt to the patent Mary Janes, and there’s something so French (read: chic) about the black and white combo Meester’s got going on. The structured bag with a silver chain strip is an unexpectedly hard accent to this sweet feminine look, perfectly appropriate for Leighton’s style.
And that wraps up our two part red carpet recap of Leighton Meester! It’s incredible timing, really, considering she is performing tonight at The Vogue with Check in the Dark. Aaand you can still get tickets for like $25. I can’t go, but you should! And then report back to me on what she was wearing.
Much love, Madison Blake