Serena (Season 1, Episode 1)
The first and most iconic outfit: Serena getting off the train at Grand Central Station looking like the well-traveled, well-heeled teen she is. The Louis Vuitton luggage, the Breton striped tee and the jaunty scarf scream, "I've been to Europe and back more times than you can count."
Blair and her minions (Season 1, Episode 1)
Beneath the sweet lace collar, gold headband and flouncy jacket lives a ruthless schemer. Blair Waldorf, it's a pleasure to meet you.
Blair (Season 1, Episode 2)
A white dress with black tights? Blair makes it work.
Serena (Season 1, Episode 2)
Serena wears the brunchiest of brunch outfits.
Serena (Season 1, Episode 3)
A tall girl like S can pull off over-the-knee boots from Chinese Laundry and a slouchy Magaschoni cashmere vest.
Blair & Serena (Season 1, Episode 4)
What's the best way to make up when you've gotten in a fight with your best friend? A photo shoot, of course. S and B play model in two bright, backless sheathe dresses by Abigail Lorick -- and for once, Serena wears the headband.
Blair & Serena (Season 1, Episode 7)
This Phillipe Adec blazer (worn with a Zara top, French Toast skirt and a Valentino bag) may be the preppiest thing Blair's ever worn.
Blair (Season 1, Episode 10)
Blair pulled off red tights (even if they were from American Apparel) with ease, pairing them with a Zara blazer, a Moschino sweater, Marc by Marc Jacobs flats and Repetto heels in hand.
Serena & Blair (Season 1, Episode 10)
If red tights are Blair's signature legwear, Serena's are thigh-highs. (Serena's sweater is Nanette Lepore and the bag is Botkier, FYI.)
Serena (Season 1, Episode 10)
For her "coming out" at cotillion, Serena stuns in a strapless gold gown with devil-may-care knots all over it. Classic.
Blair (Season 1, Episode 10)
For the cotillion episode, "Gossip Girl" costume designer Eric Daman designed Blair's dress on his own. <a href="http://www.vulture.com/2010/09/gossip_girl_-_eric_daman.html#photo=3x61597">He told New York magazine</a>, "[It] was actually the first dress I ever got to design myself for the series. I was given [an] advance notice from the producers that this was coming down the pipeline and it might be nice to design something that was extra special. So in three days we made this gown. [Blair's] mom Eleanor had supposedly designed it, and Eleanor is based on Carolina Herrera a little bit, so I was doing a little vintage Carolina. But I wanted Blair Waldorf to have this big bow, so I had a giant bow on the shoulder. I really wanted Blair’s dress to be Marie Antoinette–inspired."
Blair (Season 1, Episode 11)
Ice skating in the city requires the full uniform: a knit beret, white tights, a pink sweater and a matching plaid capelet and skirt. Oh, and pink pom-poms on one's ice skates.
Dan & Serena (Season 1, Episode 12)
Dan and Serena's all-American outfits just scream "Prep school!" (We're especially loving Serena's camel coat.)
Blair & Serena (Season 1, Episode 14)
Red, white and navy tied up with a headband = Blair at her best.
Blair (Season 1, Episode 12)
The quintessential Blair Waldorf school uniform: plaid, stripes, a necktie and a giant headband.
Blair (Season 1, Episode 13)
In the oversized headband, gold bow and swingy Alannah Hill coat, Blair looks like an American Girl doll come to life.
Chuck (Season 1, Episode 13)
Chuck goes old school in a plaid vest and a newsboy cap.
Jenny (Season 1, Episode 14)
As Jenny hits her stride at Constant Billard, she puts her own spin on Blair's preppy uniform (a Valentino coat, white Ellen Tracy tights, Juicy Couture ankle socks, Moschino shoes... and a headband).
Jenny (Season 1, Episode 14)
Jenny in all her Upper East Side glory.
Blair & Serena (Season 1, Episode 14)
Blair looks a little nun-like in her bulky coat and poofy sleeves, but Serena's leather jacket is right on target.
Serena (Season 1, Episode 18)
For her mother's wedding to Bart Bass, Serena wears a hot-off-the-runway Ralph Lauren dress (and ill-advised black gloves).
Nate (Season 1, Episode 14)
Classic Nate Archibald: untucked shirt, loosened tie, perfect man bangs.
Chuck (Season 1, Episode 14)
What is Chuck Bass without his scarves?
Blair (Season 1, Episode 18)
Only B could pull of this costume-y nautical dress by Bettie Page Clothing, paired with Yves Saint Laurent heels and Louis Vuitton luggage.
Chuck & Nate (Season 2, Episode 1)
Nate keeps things simple with mandals, but Chuck can't get dressed without at least one jaunty accessory.
Chuck & Blair (Season 1, Episode 15)
Chuck and Blair basically match here, with B in a Zara sweater, a Valentino blouse, a Ralph Lauren belt and coat, a skirt from French Toast, a Brooks Brothers bag and tights from H&M.
Chuck (Season 1, Episode 18)
No one wears a plaid vest like Chuck Bass.
Blair & Serena (Season 2, Episode 1)
While summering in the Hamptons, Blair stays preppy as always in an Alice + Olivia dress, a Susan Daniels headband, Lulu Guinness shoes and a Kate Spade bag while Serena goes casual in a Vena Cava dress, Helen Ficalora necklace, Te Casan shoes and a Chanel bag.
Serena (Season 2, Episode 1)
All dressed up for the White Party in the Hamptons, Serena looks like a Greek goddess in this Oscar de la Renta dress.
Chuck (Season 2, Episode 1)
Three words: argyle knee socks.
Chuck (Season 2, Episode 1)
For the White Party, Chuck wears an ascot, natch.
Jenny (Season 2, Episode 8)
Jenny shows off her increasingly punky/hipster side with plaid and a beret.
Serena (Season 2, Episode 6)
For a visit to Yale University, it doesn't get preppier than a striped white blazer by Ralph Lauren emblazoned with a crest... but leave it to Serena to pair it with a heavy dose of cleavage.
Chuck (Season 2, Episode 6)
Chuck steps up his style game when visiting Yale University.
Blair (Season 2, Episode 6)
Blair plays the part of Ivy League student in a L.A.M.B. skirt, an Anna Sui blouse and a hat, bag and shoes by Coach.
Agnes & Jenny (Season 2, Episode 8)
Jenny's going through a strange hair phase here, but at least her little lace Topshop dress is adorable.
Jenny (Season 2, Episode 9)
A lil' fascinator for Lil' J.
Blair (Season 2, Episode 10)
A beret <em>and</em> an ascot? Only Blair Waldorf could treat high school halls as a Parisian boulevard.
Blair (Season 2, Episode 13)
The cast of Gossip Girl are the chicest funeral-goers ever.
Blair (Season 2, Episode 24)
Blair's prom dress is center stage in this episode as Chuck gifts her her dream dress.
Blair (Season 2, Episode 25)
For her big romantic moment with Chuck, Blair goes bold with color...
Chuck & Blair (Season 2, Episode 25)
... and she gets totally swept away.
Blair & Chuck (Season 3, Episode 1)
Blair kicked off the season in a metallic frock, accented with a L.A.M.B. clutch. Oh and her boy toy, Chuck Bass.
Jenny (Season 3, Episode 7)
Nice to meet you, Jenny Humphrey's hair extensions.
Jenny (Season 3, Episode 9)
Nice pins, Little J.
Blair (Season 3, Episode 10)
Leggings as pants?!? This Blair outfit, consisting of a Theory jacket, Manolo Blahnik heels, a Chanel bag and those leggings, caught us entirely off-guard -- somehow we can't envision Blair OK'ing it for anyone else.
Serena (Season 3, Episode 11)
A sheer lace Stella McCartney jumpsuit for Thanksgiving dinner? Sure, why not.
Serena (Season 3, Episode 13)
Serena manages to look sexy even when she's totally covered up (here, it's a Phillip Lim coat, a Blugirl sweater dress, over-the-knee brown boots, DKNY plaid tights and a Carlos Falchi satchel getting the job done).
Blair (Season 3, Episode 17)
This Matthew Williamson Resort 2010 dress played a pivotal part in the episode, in which Chuck and his evil Uncle Jack conspire to seduce Blair by, in part, buying her that gorgeous dress. The episode brings out the ugly dark sides of everyone involved, but dear Lord is that frock stunning.
Serena (Season 4, Episode 1)
Love that dress, not sure about the hat.
Blair (Season 3, Episode 22)
We adore this green coat, worn with yellow Christian Louboutin pumps and a yellow Longchamp bag.
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