Gossip Girl 100th Episode Party

Posted on November 21, 2011

The most significant cultural event of the last half-century, the 100th episode of Gossip Girl, was recently celebrated as the milestone in western civilization it so clearly is at Cipriani Wall Street in New York City.  Let’s all, through the magic of the internet, pull back the veil on this historic occasion and make fun of everyone’s outfits. We already got a head start with Pocahontas Barbie earlier.


Chace Crawford

You might not think we’d say this, but we actually dig this for being low-key, classically chic. Those are chinos or jeans on the bottom, so we don’t mind the extra hem length, and the shirt and jacket look effortless but put together. The collar is lying flat and that makes us sad, but the rest of it works fine for the event.


Chloe Moretz in Stella McCartney

Oh, sweetie. Your pretend gay uncles just love watching you make these fun mistakes. Keep up the good work.


Ed Westwick

His red carpet posing is always of the utmost hilarity; his expression always hovering at the midpoint between feigned ennui and a gall bladder attack. This is not a bad look, but we don’t love those shoes.


Kaylee DeFer in Thierry Mugler

Severe. That was our first thought. It’s a pretty fierce dress. We don’t think it really needs the leopard print shoes and super tight hair. She could have softened the detailing slightly.


Kelly Rutherford in Peter Som

She looks like – and this is a little mean – one of those anthropomorphized characters representing various things left behind by your broom in those Swiffer commercials.

“I’m lint!”


Leighton Meester in Balmain

When we saw a closeup of her, we thought her hair and makeup looked pretty and hoped for similar effects from the dress. Then we got the full shot and all our hopes were dashed. In fact, we’re questioning our initial reaction to her hair and makeup. The dress is complicated and not very flattering and the shoes look cheap.


Matthew Settle

Mary, Mother of Pearl are mirrors against your religion or something? How can you not see that jacket cutting you in half? Worst proportions seen on a male on the red carpet since MC Hammer was a cultural force to be reckoned with.


Michele Trachtenberg in Rebecca Taylor

This is almost something. We think she could rock this jumpsuit – no, really – but it needs better styling than this. Smaller clutch, less doorknocker-y jewelry, and less focus-pulling shoes would help a lot, as would a less severe hairstyle and serious toning down on the eye makeup.

So apparently when we say this is “almost’ something, we mean “barely.”


Nan Zhang

We were almost ready to declare this another red lace dress of which we approve even though we hate red lace dresses (it’s been a recurring thing lately), but then we saw those accessories and now we’re so enraged that we both feel migraines coming on.


Penn Badgley

Our first impulse is to say he looks a little douchey. Our second impulse is to admit if we were attending the event, we’d probably have him pegged as one of the most put-together (if not exactly exciting) men in the room.


[Photo Credit: Mario Santoro/PR Photos]

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  • Judy_J

    I don’t know who Matthew Settle is, but that has got to be the worst look EVER.  What in the world was he thinking when he decided to pair that blue jacket with those pants?  He looks like he pulled those pieces out of the used clothing giveaway bag.  Shoes are bad, too.

    • The Love Boat song started playing in my head when I saw that. 

    • Did he borrow his 12 year old brother’s clothes?  The pants are too short, the jacket, besides the fact that the sleeves are way too short, looks like the length a waiter would wear.  By the way, who the heck is he???

    • I hate double-breasted jackets.  They just have a douche vibe to me regardless of who is wearing them, or in what context.

  • Cheri Lee

    I don’t know what it is about Ed Westwick but he is so sexy to me.

    • You sure said something there, pardner. Despite his bizarre expression, he looks like sex on a stick. 

      • Anonymous

        You meant to say barf on a stick, right?

        • Um, no. I didn’t say I was proud of my reaction, however. Sometimes the hormones do strange things to one’s perceptions.

    • If you watch the show he’s even hotter. Sometimes I question my sanity when I realize how very, very attractive I find him.

    • It’s the attitude.  He’s actually physically the least attractive male star in the Gossip Girl cast, but he’s got enough confidence for all of them and that makes him more attractive than he actually is. 

      • Anonymous

        Must be hung, that’ll do it to a guy’s confidence.  Somehow he makes smarmy a good thing.  Not to say he’s not attractive though. 

      • i definitely do not find him less attractive than Penn Badgley, who shows off how incredibly unattractive he is just above.  That curly floppy hair? Barf.

    • It’s the attitude.  He’s actually physically the least attractive male star in the Gossip Girl cast, but he’s got enough confidence for all of them and that makes him more attractive than he actually is. 

  • Anonymous

    This is the most I have ever loled at a TLo post.

  • Rand Ortega

    “I’m lint!”
    I’m crying. I’m trying so hard not to laugh, but tears are streaming down my face.
    Thank you, TLo, for starting my vacation off w/ a hilarious bang!

  • Leighton Meester’s hair and makeup is giving her full-on Minka Kelly realness.

  • Anonymous

    Nan Zhang needs to send that bag to me.  I’d love it and accessorize it properly.  Mind you, I’d probably also use it to give people a “Kabooong” over the head when they annoy me.

  • Ed Westwick.  How could you guys have let him slide by with those crazy bad fitting pants with the gapping zipper fly?  What a douchey mess.

    And Leighton?  Please go to the loo and comb your hair.

    • Anonymous

      Am I wrong or are Ed Westwick’s shoes unbuckled? ON PURPOSE?

      • Anonymous

        Yes! They are! I know fashion needs sacrifices, but having to cling to your shoes with your toenails does not sound like an effort a boy should make for *fashion*. What’s next, undone shirt? Oh, wait, we saw that already… 

      • Lordy, I hadn’t noticed that on my own. What a hot steaming mess.  If he calls, I am SO not available for a date.

    • Anonymous

      douche bag was my first thought as well. 

      • Anonymous

        And my second and my third thought as well…

    • Anonymous

      I’m kinda into the jbf hair she’s rocking. It’s sexy.

      • M’kay.  I get that. And I can even see it working a bit.  My only quibble here is that we are on the red carpet.  Should you look like you just climbed out of the sack with your latest shag, in order to have your picture taken?  I get it that it is a music awards presentation so the same rules don’t apply as to the Oscars, but come on now; is a comb too much to ask?

        • Anonymous

          I don’t like that kind of hair when it’s too messy, dirty/grungy looking, or contrasts too much with the outfit, but in this case it all works. She’s got on a dress that’s sexy, edgy and complicated, so jbf hair makes sense. I think soft, undone hair might have worked as well, but I think she would have sooner picked severe hair because she wouldn’t want to make the whole look too sweet, and no matter how much cleavage it’s hard not to look sweet in a white dress.

        • Um, it’s not a music awards presentation… it’s just a party. Is her hair okay now?

          • Oops, that’s what I get for looking at too many of these posts in rapid fire sequence.  I start getting my in/out, RC, party, photoshoot stuff confused.  mea culpa!

            Well, hell, if its just a party then let it all fly!

          • Yeah I kind of hate her dress, but I forgive the jbf hair since it’s a party. Rock your messy hair, girl.

    • Anonymous

      Oh God, that zipper! It was the first thing I noticed because erm, well it was the first thing I noticed!

      • Nothin’ wrong with noticing a nicely packed crotch.  Do it all the time.  lol

  • Anonymous

    WHAT ARE THESE PEOPLE DOING. New York is one of the most stylish cities in the world. Surely, they could have come up with something better than this.

  • Anonymous

    Go with your first impulse on Penn.

    • Anonymous

      He had me on his side until I saw the shoes WITHOUT LACES. Just…no.

      • Anonymous

        And why are his shoes so long?  Does he have flat extended toes?

  • Jessica Rowe

    I actually adore that Stella McCartney.  ADORE it.

  • Kaylee DeFer looks like an Escher drawing. Nan Zhang looks like the living embodiment of Red Hots candies, and not in a good way but rather in an artificially flavored spiciness sort of way. 
    Aaaand that’s all I’ve got. 

    • Anonymous

      Great Halloween costume ideas for next year!  Thank you!

      • Bonus points if you manage the Atomic Fireball purse. 

  • C.

    Chloe!  Honey!  Enough with the duckface. 

  • Anonymous

    no, her hair & makeup do look good. makeup’s a little shiny but hair is so nice it makes up for it. dress, though, oh heavens what is balmain up to w/ that?

    she only looks like lint on the sides. & it’s more like the cat hair from the bottom of the vacuum cleaner.

    why does the kid in stella mc have strings tied around her ankles?

    the little round red purse is better than all the rest of it; a lot of the red lace these days is fine, this looks like cheap 80s overdyed.

    needs the big clutch to cut the monotony of the jumpsuit. actually, i think its styling are what’s making it look tolerable. all of the other stuff is so, as you say, focus-pulling that it turns that solid navy blue tankenstein into more or less a backdrop. she coulda found more interesting things to put against it, true, but the concept is solid.

    that thierry mugler is so heartrendingly fabulous that it’s a shame to see it accessorized w/ cliché & non-matching in any way, bad or good, leopard [of all things].

    the two guys, westwick & the last one, look better than the third, the half-chopped one. the first one i’ve already forgotten about & if there were more i’ve even forgotten they were there. were i twelve years old i woulda thought the last one rather attractive. then again, i’m not.

  • I actually think Nan Zhang looks pretty good.  Legitimately sexy.  Even with all the excessive red-ness.  But wasn’t that girl studying neurology or something at John Hopkins?  I thought she has better things to do than with a show that forces her to be a mime (despite the fact she can clearly act better than half of the cast; she at least has more than two expressions).  But then again, what girl is going to say no to free dress and a chance for photography?

    Oh Leighton, you have such a classical beauty’s face.  Only if you dress for it.  Get these people for styled you for Vera Wang immediately!

    Chace always dress well.  Too bad he acts worse than Blake Lively, and that is really saying something. 

    It’s kinda sad to see how Gossip Girl went from a massive guilty pleasure to many people to a show no one cares about. 

    • Anonymous

      Stop saying everything I think, and saying it better. Stop, I say. Stop! 

    • Anonymous

      Gossip Girl went to hell so hard.

    • Anonymous

      I don’t know, that red lace dress looks like all the stripper dresses I used to sell at a shop on Haight Street back in the 80s. All she needs are some pointy toed boots with skulls for buckles and it would be 1985!

  • About Michele Trachtenberg, I would have said that her “clutch” which looks like a folded up door mat goes with the door knocker necklace — for an overall look of a house entrance?  eh.

    • Anonymous

      Aw, I like the clutch!  It makes me think maybe she brought a book on case she gets bored, which is what I always want to do.

  • But where’s Taylor Momsen? Can we really have a Gossip Girl event without a micromini, shredded stockings, and eyes ringed in eyeblack?

    • She “quit acting” so something tells me teen street walker didn’t feel like showing up.

  • Anonymous

    Ed Westwick seems almost as smarmy in real life as Chuck Bass, so maybe he is just being himself on the show. I think Leighton Meester is very beautiful and I can never understand her fashion choices. But they all look great compared to Matthew Settle, who chose to dress as Peewee Herman for this very special event.

  • Sling a guitar around that Zhang chick’s neck and she could totally be in Wayne’s World singing “Ballroom Blitz”.

    • Anonymous

      And her name was Cassandra…Schwing

  • Anonymous

    Chloe – wth

    Kaylee’s dress – really is great
    Kelly looks olfer than she is and expect certain comments about that fur/feathers
    Leighton – I don’t think the shoes look cheap.

    Matthew – ???????

  • Anonymous

    Does every single one of these guys have a hand in his pocket? I think so. Well, except one, and he’s disqualified.

  • I love that jumpsuit – so much better than slutty dresses.

    • Anonymous

      I think we’ve come to like them because they are not another slutty dress. Am I a prude or have people lost all objectivity on  skank fashion (esp shoes)? 

    • Anonymous

      Agreed, I think Michele looks fierce! The necklace and shoes really help to distract you from the jumpsuitness of the outfit, if you know what I mean. And I hope you do.


  • Anonymous

    Bless Chase Crawford for wearing a jacket that FITS! He looks fine — I’ll forgive the flat collar because, hey, it happens when you move around. He looks relaxed and comfortable, from his pocket square down to his nice, polished shoes. Very effortlessly put-together, indeed. He poses well.

    I like Chloe Moretz in the Stella McCarney– she’s 14 and can pull it off. Her hair, however, should have been combed.Ed Westwick’s look IS bad. Somebody please tell him that when the tape of a zipper shows, the trousers are too tight. So is the jacket. If everything fit properly, then it might be “not bad.” (But that ‘tude! Woof.)

    Leighton Meester’s whole look is cheap.
    Matthew Settle should have been sent home with a note.

    I hate the overly worn-in, laceless shoes that so many guys are wearing on the red carpet. What a silly affectation.

  • Anonymous

    Matthew Settle WTH? LMAO! Kelly Rutherford, lint tumor. Michele Trachtenberg STILL doesn’t get it right.

  • Anonymous

    I love that Nan Zhang is carrying a little Pokemon ball. I wonder who’s in it? 

    Matthew Settle looks so pleased with himself in his itsy jacket and big boy clothes that someone should give him a lollipop.


      Every time I scroll up to look at Matthew Settle’s photo, l’m overcome with laughter. It’s sooo goood.

  • Anonymous

    The Swiffer reference alone made this worth reading!

  • Anonymous

    To hell with Nan Zhang’s matching accessories, the bitch is fierce.

    • she’s got exactly the right figure for that dress. I can ignore the accessories

    • Helen C

      That girl (and the gorgeous black model who played Iz) is so under-used in this show.  And the producers’ excuse is “we can’t find a black actress or an Asian actress who’s funny and can act.”  Which is such a huge bull-sh*t.  Iz and Katy pretty much steal every scene they are in.  They have so many different expressions and can actually enunciate their lines.  That is way better acting and more talents than Blake Lively and Chace Crawford combined together.  

      • I kind of find it hard to believe that the producers would dare to openly use “we can’t find a black actress or an Asian actress who’s funny and can act” as an excuse.

  • I actually like the Chloe Moretz outfit. It’s kooky and age appropriate, for once. 

    Penn Badgely looks cute. 
    Michelle Trachtenberg = win

    Kaylee DeFer – too bad about the leopard shoes. Should have been something less attention-pulling with that dress. Woulda worked if she’d gone for something black and more simple. 

  • Anonymous

    Penn Badgely? Looking douchey? Never! (/sarcasm)

    Poor guy. I have no sense of whether he actually IS douchey. He’s just one of those guys that naturally LOOKS douchey.

  • foodycat

    If Badgley is a suicide risk, they should take away his scarf as well as his shoelaces.

  • Anonymous

    Dawn (whoops, I mean Michelle Trachtenberg) needs a contrasting belt – that would go a long way to making this jumpsuit work. I do love the navy color, and that necklace is pretty bad-ass.

    She will always be Dawn to me. Shut up, Dawn.

  • michelle shields

    I have no clue who any of these people are. And I really don’t care! lol

  • Anonymous

    if we were attending the event, we’d probably have him pegged as one of
    the most put-together (if not exactly exciting) men in the room.

    Well, sure.  It’s not like there was a lot of competition.

  • MilaXX

    I don’t know how you guys do it, I’m tired of ripping celebs today. I will say I think Chloe looks cute except for the light ankle straps & Michelle would be passable if she kept the shoes, removed all the jewelry removed except for one ring, let her hair down and changed bags. I cannot begin to say how sad it makes me that Penn is the best dressed of the lot.

  • Ali

    Penn Badgley looks a bit Hugh Dancy-ish with his longer hair. I never noticed it before.

  • Anonymous

    TLo, you guys are such good writers! I know Tom does most of the writing, but I love both daddies equally. This post is so nicely crafted and hilarious. A pleasure to read (and snark along).

  • Anonymous

    “the 100th episode of Gossip Girl, was recently celebrated as the milestone in western civilization it so clearly is”
    LOVE you guys for this

  • Anonymous

    And to think, the costumes on this show are amazing.  Leighton Meester and Kelly Rutherford’s characters (heck, even Matthew Settle’s character) look so well put together.

    • Anonymous

      I think the some of the actors are trying to distance themselves from their characters, but if what their characters usually wear is classic, elegant, flattering clothing then distancing themselves necessarily entails heading into dubious territory. Chace looks just like Nate in the above picture, might even be wearing his actual clothes and he looks great. In fact, all of the ones that look good look just like their characters. Kind of a catch-22 when you’re on a show where the characters regularly wear red carpet wear.

  • Anonymous

    I don’t know who half of these people are, as usual…but Kayley’s dress is absolutely FIERCE.  I love it.

    Obviously Chloe’s dress is from that same Stella-was-on-crack collection as Gwynnie’s.

    I don’t know Penn either (I’ve read/heard the name somewhere)…but I would LOVE to get my hands all tangled up in that hair.  Mmm.

  • Anonymous

    Nan Zhang is wearing a restaurant hostess dress, no? Ugh. I don’t like ANY of the looks (male or female) in this RC post, but I dislike hers the most. 

  • Anonymous

    Westwick always looks like Pattinsons “special” brother. Penn looks pretty adorbs as does Crawford

  • Anonymous

    Ed Westwick always reads “douchey, preppy, pretentious frat boy” to me. Ick.

  • Anonymous

    I’ve never seen this show but that Matthew Settle person has me just DUMBFOUNDED. I just know he’s going straight to his second job sitting in Paul Lynde’s square on “Hollywood Squares” after this party. Or maybe he’s going to appear on “Match Game ’75.” There’s something very Charles Nelson Reilly about his get-up, if he only added a little neck scarf. 

  • Anonymous

    Where is Miss Blake?

    • Anonymous

      never mind.  that outfit definitely deserved a post of it’s own.  yikes

  • Is it just me or is Penn Badgley (who is super cute a lot of times) giving off a sort of James Franco vibe? Hmmm…

  • Sarah Asarnow

    Leighton Meester’s dress is so Ariel the Little Mermaid’s “I have legs now!” dress made out of ships rigging. If she were a stripper.

  • Anonymous

    Kelly Rutherford should really get that mole removed.

  • Anonymous


    That is all.

  • Allison Woods

    I love that Thierry Mugler black dress even if the hair and shoes are not right. Looks fab on her to boot.

  • Anonymous

    ‘I am lint’ = genius.

    Why is Michelle T’s bag so big? Was she smuggling someone into the party? I’ve gone away on overseas trips with less luggage!

  • Gossip Girl is still on?

  • Poor Matthew. Looks like he’s wearing his son’s private elementary school blazer. Kelly has gray feather saddlebags growing from the front of her dress. FAIL.