Iconic Style Moments From Five Years of Gossip Girl

Season/Episode: 1-1 Even today, the main titles begin with Kristen Bell whispering about Serena’s mysterious whereabouts, accompanied by a shot o... Season/Episode: 1-1 Even today, the main titles begin with Kristen Bell whispering about Serena’s mysterious whereabouts, accompanied by a shot of her returning to the Upper East Side in a really cute coat, actual normal-person pants, and … a striped high-necked shirt. Given Serena’s later allergy to covering her sternum, this is remarkable. She must have wandered off a Law & Order set.

Season/Episodes: 1-1, 1-7, 1-16 In the first season, Blair rarely appears without a bow sprouting from her head, like the ribbon crowning the won... Season/Episodes: 1-1, 1-7, 1-16 In the first season, Blair rarely appears without a bow sprouting from her head, like the ribbon crowning the wonderful wrapped gift that is her personage. Those headbands became so ubiquitous that they actually have their own Facebook page. They are the perfect accessory for Blair, encapsulating both her twee cutesy side as well as the part of her that would rather die than look anything less than the epitome of a private-school social princess, even if the trappings of that persona make her want to roll her eyes.

Season/Episode: 1-1 Hey, remember when this show featured realistic school uniforms, and Little J wasn't wearing a metric ton of coal smeared aro... Season/Episode: 1-1 Hey, remember when this show featured realistic school uniforms, and Little J wasn't wearing a metric ton of coal smeared around her eyes? Neither do we, but here's photographic proof that it happened. So far removed are we from these days that this actually looks like an outtake from another show. Maybe some British thing about boarding schools?

Season/Episode: 1-16 "A masquerade, how novel!" we cheered at the time. How innocent we were: Five seasons later, it feels weird if a G... Season/Episode: 1-16 "A masquerade, how novel!" we cheered at the time. How innocent we were: Five seasons later, it feels weird if a Gossip Girl shindig doesn't involve ball gowns, Eyes Wide Shut masks, and mistaken identities. Here, at the inauguration of this tradition, Jenny looks refreshingly (and nostalgically) normal, but it's comforting to know that Blair's flair for Breakfast at Tiffany’s–accented drama is innate, as is Serena's tendency to show up places looking like a bird.

Season/Episode 1-17 First Blair treats Chuck Bass to a scandalous striptease at the Victrola, then to her virginity in his limousine. Only Blair ... Season/Episode 1-17 First Blair treats Chuck Bass to a scandalous striptease at the Victrola, then to her virginity in his limousine. Only Blair Waldorf would take herself by surprise with both those developments while conveniently sporting under her ladylike clothes the major lingerie necessary for both activities.

Season/Episodes: 1-18, 2-1, 2-12 Chuck Bass became to Gossip Girl what Nolan is to Revenge and Lavon is to Hart of Dixie: the purveyor of colorfu... Season/Episodes: 1-18, 2-1, 2-12 Chuck Bass became to Gossip Girl what Nolan is to Revenge and Lavon is to Hart of Dixie: the purveyor of colorfully entertaining ensembles that make you realize, despondently, that you don’t have enough male argyle, scarves, or sparkle in your life. In later seasons, when he becomes an unlikely mogul who speaks only from the very back of his throat, we mostly got funky ties and pocket squares under fancy suits. But early on — and did anyone remember his hair was so demi-Bieber? — Chuck was bold. He liked it bright and tight, like a Disney starlet dipped in preppy douche.

Season/Episodes: 2-4 and 2-10 Whither the Constance Billard student handbook, Headmistress Queller? Blair looks like she's attending a completely... Season/Episodes: 2-4 and 2-10 Whither the Constance Billard student handbook, Headmistress Queller? Blair looks like she's attending a completely different institution — perhaps a French one that produces the world's finest mime clowns — and Serena isn't even trying with that limp necktie and undershirt. The wardrobe department's lackadaisical take on the school's uniform code will, of course, eventually be mirrored by the writing staff's lackadaisical take on the concept of school in general.

Season/Episode: 2-4 What, you expected Umbros and Hard Rock Café tees? Of course gym class at Constance looks like this: loads of jewelry ... Season/Episode: 2-4 What, you expected Umbros and Hard Rock Café tees? Of course gym class at Constance looks like this: loads of jewelry and expensive midriff belts that match each person’s headgear and socks. This is what the Williams sisters would look like if they played field hockey.

Season/Episode: 2- With one season under its belt, Gossip Girl launched headlong into New York Fashion Week with an Eleanor Waldorf show. The res... Season/Episode: 2- With one season under its belt, Gossip Girl launched headlong into New York Fashion Week with an Eleanor Waldorf show. The result: a hilarious seating chart that put Anna Wintour in worse seats than both of us and former Top Model winner Naima, and this amazing shot of approximately five photographers at the end of a NYFW runway, a paucity which would only happen if the rest of the fashion press were drugged and locked in a closet. But the big moment in the episode was Little J’s debut: A jealous Blair sent Serena down the runway wearing one of Jenny’s designs, which accidentally ended up legitimizing Jenny — when clearly it should’ve ruined Jenny's life, because Serena looks like a cross between Betsey Johnson and an electrocuted Granny Smith apple.

Season/Episode: 2-9 Hello, Jenny's eyeliner. We have not missed you at all since Little J got the boot. Nor have we missed her penchant for bizar... Season/Episode: 2-9 Hello, Jenny's eyeliner. We have not missed you at all since Little J got the boot. Nor have we missed her penchant for bizarre accessorizing, like this depressing homemade fascinator and her emo hooded-blanket-poncho. The hooblaponch: The perfect item to pull out of your closet when NO ONE UNDERSTANDS YOU, and extra appropriate when you both prefer to look homeless and briefly are.

Season/Episodes: 2-11 and 3-11, A.K.A. Thanksgiving on the Upper East Side By now, Serena has started displaying her … special … sense of oc... Season/Episodes: 2-11 and 3-11, A.K.A. Thanksgiving on the Upper East Side By now, Serena has started displaying her … special … sense of occasion. Family holiday gatherings are the perfect venue for satin sausage-casing skirts. (No room for turkey and mashed potatoes, but Serena probably sticks to wine anyway.) And who hasn’t broken bread with their loved ones wearing a plunging black jumpsuit with illusion lace? We’re sure Blair gave thanks for that one, as her lovely frock contrasts sharply with Serena’s heinous outfit. Does that thing transform into a wetsuit? Because it looks like one from the back. Then again, Serena did run off with Nate’s congressman cousin after this, so maybe "scuba diving” is a saucy euphemism on the Upper East Side.

Season/Episode: 2-18 In which Serena and Blair end up starring in the Constance production of Age of Innocence and — echoing the previous season'... Season/Episode: 2-18 In which Serena and Blair end up starring in the Constance production of Age of Innocence and — echoing the previous season's masked ball — Blair looks dramatically long-suffering while Serena looks like she's the spokesmodel for Avian Flu.

Season/Episode: 2-24 It’s prom night, and rather than a 90210-style Brenda and Kelly identical dress debacle, S and B go in opposite directions: ... Season/Episode: 2-24 It’s prom night, and rather than a 90210-style Brenda and Kelly identical dress debacle, S and B go in opposite directions: Serena’s dress is tasteful and understated, two adjectives one rarely associates with her in the latter seasons of Gossip Girl. But Blair wins the day in a stunning statement Marchesa gown embodying everything that label used to do so well: flattering structure with romantic detailing that enhances rather than overwhelms. Sure, this dress had already been worn by Dita Von Teese (and Georgina Chapman herself), which you’d think would be a turnoff for Blair, but then again, she did first attract Chuck with a burlesque performance and she's prone to cranial accessories. Maybe Dita is her spirit animal.

Season/Episode: 3-4 and 3-9 Jenny rebounds from her tragic homeless designer shenanigans and into Blair’s spot as the Constance Queen Bee, which ... Season/Episode: 3-4 and 3-9 Jenny rebounds from her tragic homeless designer shenanigans and into Blair’s spot as the Constance Queen Bee, which apparently necessitates altering her uniform so she looks like she’s in a motorcycle gang called Hell’s Cater Waiters. She also, at her cotillion, sports idiotic half-gloves, which is something Paris Hilton has done. Little J is officially the worst at life.

Season/Episode: 3-1 and 3-16 Perhaps because the writers couldn’t handle the vast numbers of grown women in the real world who started wearing he... Season/Episode: 3-1 and 3-16 Perhaps because the writers couldn’t handle the vast numbers of grown women in the real world who started wearing headbands in her honor, Blair moves onto hats when she becomes an NYU student. While it seems deliciously in-character for Blair to think this is a maturation in decorative headgear, it’s adorable that she thinks dressing like every day is Derby Day is exactly the best way to fit in there.

Season/Episode: 3-17 Dear Blair: Your Matthew Williamson gown is beautiful, and we’re happy the silver lining to your Indecent Proposal moment wa... Season/Episode: 3-17 Dear Blair: Your Matthew Williamson gown is beautiful, and we’re happy the silver lining to your Indecent Proposal moment was that you look great while being humiliated. But Blair of all people believes in going full-bore with a theme, and so, knowing she has to sleep with Chuck’s nefarious uncle so he’ll return ownership of a hotel to Chuck, we are surprised Blair chose a classy goddess-like nightie — the type of thing she’d want to wear for an actual good memory — instead of some ruthlessly functional naughtywear that she could burn later without remorse.

Season/Episode: 3-22 Because nothing says, "Surprise! I'm passing off my Russian mafioso's baby as Dan Humphrey's!" like gold lam&eacut... Season/Episode: 3-22 Because nothing says, "Surprise! I'm passing off my Russian mafioso's baby as Dan Humphrey's!" like gold lamé American Apparel cast-offs repurposed as maternity wear for the terminally dramatic. Oh, Georgina Sparks, you inept little schemer, you are a constant delight. Never change.

Season/Episode: 3-22 You might think that Jenny having sex with Chuck represents the nadir of her character, but we think that honor belongs to t... Season/Episode: 3-22 You might think that Jenny having sex with Chuck represents the nadir of her character, but we think that honor belongs to the moment she decided to staple the world's rattiest extensions to her scalp. Seriously, she got those out of a plastic bag clipped to the wall at Party City. Get a hold of yourself, Little J.

Season/Episode: 3-22 Which was more shocking: the season-ender in which Chuck Bass was shot and left for dead, or the fact that he didn’t even lo... Season/Episode: 3-22 Which was more shocking: the season-ender in which Chuck Bass was shot and left for dead, or the fact that he didn’t even look snazzy while bleeding out all over the pavement? True, he was depressed due to the latest implosion of his relationship with Blair, but he was also drinking to forget her. Shouldn’t he have been sporting some party plaid? Devil-may-care sweater-vests? Get a hold of yourself, Chuck.

Season/Episode: 4-1 Bless you, Blair Waldorf, for remembering to pack a beret into your many, many Parisian-bound suitcases. And bless you, Seren... Season/Episode: 4-1 Bless you, Blair Waldorf, for remembering to pack a beret into your many, many Parisian-bound suitcases. And bless you, Serena van der Woodson, for deciding to sport sensible shoes for walking the city — even if you are wearing them with a dress that is, in part, a metallic Easter basket.

Season/Episode: 4-1 Blair spends her Parisian sojourn looking as bright as a Monet at times, and as tasseled and dramatic as a Moulin Rouge dance... Season/Episode: 4-1 Blair spends her Parisian sojourn looking as bright as a Monet at times, and as tasseled and dramatic as a Moulin Rouge dancer at others. Apparently the shopping is put to good use: After the Paris episode, Blair’s style turns toward the bright and floral, as if she took the girlyness she used to pour into her headwear and finally channeled it below the neck.

Season/Episode: 4-1, 4-2 Serena, on the other hand, decides that what the City of Lights is really lacking is a direct view of her bra. The good ... Season/Episode: 4-1, 4-2 Serena, on the other hand, decides that what the City of Lights is really lacking is a direct view of her bra. The good news is that her handbag is big enough to contain a change of clothes, which means she can also eighty-six those Old Lady in Palm Beach pants. Serena Van Der Woodson is not about pants. She's about legs. Clearly, the jetlag got to the part of her brain that dresses her every morning.

Season/Episode: 4-2 We’ve long suspected Blair is the writers’ favorite person to script, and that affection seems to trickle into her wardrobe. ... Season/Episode: 4-2 We’ve long suspected Blair is the writers’ favorite person to script, and that affection seems to trickle into her wardrobe. When it counts, costume designer Eric Daman delivers: Blair just happens to be wearing a gut-wrenchingly stunning Oscar de la Renta gown when Serena shows up to drag her to a romantic, well-written, and poignant night-time conversation with undead Chuck, in which she lovingly releases him while he is dressed like he just went clam-digging. It’s red, like the color of her heart. Excessively ruffled, like the details of her soul. Perfect and iconic.

Season/Episode: 4-8 This is the Serena we’ve come to know and roll our eyes at in latter-day Gossip Girl: More fabric dangling uselessly from her... Season/Episode: 4-8 This is the Serena we’ve come to know and roll our eyes at in latter-day Gossip Girl: More fabric dangling uselessly from her waist than on her actual body.

Season/Episode: 4-9 Nobody loves masked hijinks more than Gossip Girl, especially if it involves mistaken-identity kisses and/or nobody being abl... Season/Episode: 4-9 Nobody loves masked hijinks more than Gossip Girl, especially if it involves mistaken-identity kisses and/or nobody being able to tell the difference between Serena and Little J. Here, they even throw Katie Cassidy’s Juliet into the mix, all in aid of tricking everyone into thinking an ostracized Serena went on a drug bender. Conveniently, Serena selected a forgettable, flappy blue gown that revealed as little of her legs and cleavage as possible, to give Jenny and Juliet the best chance at passing for her. It’s such a blessing when people break character just in time to abet revenge shenanigans.

Season/Episode: 5-1 Serena briefly flirted with the movie business … which is to say, she briefly flirted with a bunch of people in the movie bus... Season/Episode: 5-1 Serena briefly flirted with the movie business … which is to say, she briefly flirted with a bunch of people in the movie business, then got an unlikely promotion, and then flamed out because she’s unqualified to do basically anything except brush her hair (and even that … ). As such, she dressed for her role as a P.A. with all the commitment one would expect from her: a crotch-length dress, heeled mules, and a seven-pound statement necklace. If all P.A.s on the Gossip Girl set are required to dress like this, then we can say with certainty they are underpaid.

Season/Episodes: 5-6, 5-8, 5-9 Now knocked up with a royal fetus, Blair develops a fetish for headgear again. Our favorite was the tiny neon fasc... Season/Episodes: 5-6, 5-8, 5-9 Now knocked up with a royal fetus, Blair develops a fetish for headgear again. Our favorite was the tiny neon fascinator — as if she had bought a hat for the baby and then decided she couldn’t resist wearing it herself.

Season/Episode: 5-8 There is a theory that some brides make their bridesmaids wear hideous gowns to ensure that the bride is the most beautiful w... Season/Episode: 5-8 There is a theory that some brides make their bridesmaids wear hideous gowns to ensure that the bride is the most beautiful woman in the room. But what theory explains why Serena would go to Blair’s baby shower in a dress that provides curtains to her upper thighs? Seriously, those look like French doors to her fetal canal down there. Is she trying to be literal? Or does Serena actually think childbirth looks like swanning out of the elevator at the Plaza?

Season/Episode: 5-10 Blair is a drama queen, so she’d totally leap to major maternity wear even though moments prior she’d been pin-thin and invi... Season/Episode: 5-10 Blair is a drama queen, so she’d totally leap to major maternity wear even though moments prior she’d been pin-thin and invisibly pregnant. But for the pivotal episode in which she decides to leave limp Prince Louis for Chuck and then the baby dies when their limo is run off the road (let’s not even discuss how inappropriately Princess Diana that is), the show stuck Blair in a mini-muumuu that, we imagine, matches the wallpaper in the Waldorf penthouse’s downstairs half-bath.

Season/Episode: 5-10 Chuck is comatose; Blair is mid-miscarriage. For this iconic moment, Dan looks like a lumberjack, because he’s Dan, but of c... Season/Episode: 5-10 Chuck is comatose; Blair is mid-miscarriage. For this iconic moment, Dan looks like a lumberjack, because he’s Dan, but of course Serena had just come from her fake-cousin’s coming-out party and is therefore dressed like she’s supposed to pop out of the cake at said shindig. It’s memorable precisely because it’s so predictable: By this point, Serena has become adroit at coping with tragedy while simultaneously wrangling her erogenous zones to avoid any X-rated accidents.

Season/Episodes: 5-11, 5-12 As Blair’s doubts increase about her nuptials to Prince Louiiiiis (seriously, between this dude and Elizabeth Hurley,... Season/Episodes: 5-11, 5-12 As Blair’s doubts increase about her nuptials to Prince Louiiiiis (seriously, between this dude and Elizabeth Hurley, this show has a knack for hiring people whose real accents somehow sound like stilted, inept fakes), so does the size of her beanies. Perhaps she is trying to contain the thoughts threatening to erupt out the top of her skull, or these are satellites she’s using to seek advice from the alien overlords who built Louis out of some planks and a baguette.

Season/Episode: 5-13, A.K.A. the hundredth episode camptacular Yet another shining example of Gossip Girl’s renowned subtlety and complex symboli... Season/Episode: 5-13, A.K.A. the hundredth episode camptacular Yet another shining example of Gossip Girl’s renowned subtlety and complex symbolism. It's worth noting that this is more fabric than Serena has had on her body at one time in perhaps the last five seasons combined.

Season/Episode: 5-13 When Georgina Sparks started on Gossip Girl, she was an ill-planned plus-one in a dumb storyline about how men die when they... Season/Episode: 5-13 When Georgina Sparks started on Gossip Girl, she was an ill-planned plus-one in a dumb storyline about how men die when they mix drugs with Serena’s vagina. But she became so much more: In the 100th episode, she popped up in a fascinator best described as Edith Wharton Goes to Ascot to wreak havoc on Blair’s royal wedding. This also involved dressing up as an altar boy, attempting to seduce the groom on church property, and bribing a priest while standing next to a Port-a-Potty in that majestic cranial outcropping. Sometimes, we think Michelle Trachtenberg is the only person aware of what this show ought to be. Can they please ship her over to liven up Revenge? Madeleine Stowe needs a proper cohort.

Season/Episode: 5-13 It’s not that Blair looks bad in this gown; in fact, it’s perfectly beautiful as she flees the church, wearing it and weepin... Season/Episode: 5-13 It’s not that Blair looks bad in this gown; in fact, it’s perfectly beautiful as she flees the church, wearing it and weeping. No, we object to the fact that for her big wedding to a prince — her royal affair, her Middleton moment — there is no way, in even the most desolate reaches of this planet, that Blair would consent to getting hitched sporting ratty, beachy, back-brushed hair. It’s so out of character, they should have opened the next episode with her getting checked for a brain tumor.

Season/Episode: 5-13 Is it wrong that we're surprised Blair let bridesmaid Serena look so va-va-va-voom, and gave her a kicky fascinator? We alwa... Season/Episode: 5-13 Is it wrong that we're surprised Blair let bridesmaid Serena look so va-va-va-voom, and gave her a kicky fascinator? We always assumed she’d get her ultimate revenge by pouring S's assets into a dumpy bag. Forget the aforementioned brain tumor, this whole thing should have had all Blair’s loved ones checking her into a psych ward.

Season/Episode: 5-14 Poor B. After marrying Louiiiis and then finding out he made her go through with it out of spite, and thus plans to make her... Season/Episode: 5-14 Poor B. After marrying Louiiiis and then finding out he made her go through with it out of spite, and thus plans to make her miserable (which was a good twist, we admit; fictional spite-nuptials are the best) Blair fled the reception in her gown, then had to deflect media attention from herself by masquerading as a Regular Person via whatever she could find at the airport. It’s notable both for how we’ve never seen Blair look so ordinary, and for how surely no airport in the New York City area has ever been that empty.

Season/Episode: 5-15 This moment may not seem like a big deal — a run-of-the-mill plot about how Serena is mad at Blair again for the pompous ass... Season/Episode: 5-15 This moment may not seem like a big deal — a run-of-the-mill plot about how Serena is mad at Blair again for the pompous ass least worth fighting for, Dan — but it showcases how divorced this show is from sanity in its twilight years. Suddenly Blair, she of the silky nighties, is sleeping in shorts and a men’s PJ shirt while Serena goes to bed in a sequined vest? Unless she’s sneaking out the window in an hour to assist a magician at his 2 a.m. show, this makes about as much sense as beautiful-but-brainless Nate becoming a media mogul.

Season/Episode: 5-19 This is obviously the best thing that ever happened on this show. Or any show, ever.

Season/Episodes: 1-1 and 5-24 Serena ends season five on a bender; Blair ends it with Chuck at a casino. But it might be Dan Humphrey who suffers... Season/Episodes: 1-1 and 5-24 Serena ends season five on a bender; Blair ends it with Chuck at a casino. But it might be Dan Humphrey who suffers the most, going from a buzz-cut, self-effacing cutie to a smug accidental author with hair so wild and thorny that even a bird would deem it inhospitable to raising a family. Quoth the raven, “Holy shit, dude.” We hope tonight's episode opens with him getting a haircut. Bring on season six.

Iconic Style Moments From Five Years of Gossip Girl

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