Spotted: Serena van der Woodsen returning to Manhattan after a mysterious stint at boarding school. She definitely puts her own stamp on the schoolgirl look with a loosely knotted plaid tie and riding boots.
2 of 20 The CW
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Little J is the belle of the masked ball in a gold cat mask, a yellow ruffled gown and fur stole. Nate is dressed as a mysterious Phantom of the Opera, but we all know his mystery: He's still hot for Serena.
3 of 20 The CW
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Georgina Sparks is back in town to stir up trouble for Serena. Her oversized glasses and layered accessories are the perfect outfit in which to wreak havoc.
4 of 20 The CW
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Serena and Nate pretend to be dating out in the Hamptons to cover for Nate's dalliance with an older, married woman. Too bad — just look how good they look together at the White Party.
5 of 20 The CW
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After working like a dog for a famous author all summer, Dan takes a weekend at the beach with Serena, His outfit of choice: a wife-beater and khakis.
6 of 20 The CW
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Serena makes an entrance at the Snowflake Ball in a low-cut ball gown chopped short in the front, accompanied by her new flame Aaron Rose.
7 of 20 The CW
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Vanessa looks mighty seductive posing on the bed in a strapless dress. But isn't Chuck supposed to be the one seducing her in one of Blair's revenge schemes?
8 of 20 The CW
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Serena fills in at the last minute for Eleanor Waldorf's runway show, but isn't that Little J's design?
9 of 20 The CW
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While Blair and Serena fight for a place in Yale's freshman class, Chuck wears his best tweeds to New Haven to impress the school's secret societies.
10 of 20 The CW
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Poor little J. All she wants is a small birthday party, but Serena and Poppy turn it into a huge social event. Her sparkly gold top is neither sweet nor appropriate for a 16-year-old.
11 of 20 The CW
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In an '80s flashback episode: Lily (Brittany Snow) gets kicked out of boarding school and reconnects with her sister Carol (Krysten Ritter). Love the polka dots; too bad CW didn't love the idea of a spin-off.
12 of 20 The CW
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Blair and Chuck could at least crack a smile at Rufus and Lily's wedding — I mean, Sonic Youth plays! — but they're a little self-involved as usual.
13 of 20 The CW
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Serena looks happy in a navy miniskirt and stilettos, but she is clearly still skeptical about Carter.
14 of 20 The CW
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Famous actress Olivia Burke (Hilary Duff) enrolls at NYU seeking normalcy, but ends up bunking with Vanessa, warring with Blair and hooking up with Dan (and Vanessa, but that's another story). How normal is that?
15 of 20 The CW
Lovebirds Lily and Rufus look ravishing in formalwear. But has Lily remained faithful? Has Rufus?
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Vanessa cleans up well to vie with Blair for the honor of delivering the NYU freshman toast — in hopes of winning her mother's approval.
17 of 20 The CW
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Chuck launches his new nightclub with a Roaring Twenties party, but Blair does more damage than good when she secretly tries to "help" him with it.
18 of 20 The CW
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Whoa, Little J! Does a Queen Bee wear short-shorts and fishnets? What would B. say? No wonder Eric loses his patience with you.
19 of 20 The CW
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The most awkward Thanksgiving ever starts when Maureen discovers Tripp's infidelities with Serena. But what she should feel awkward about is wearing that top to a family dinner.
20 of 20 The CW
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It's been a long time coming, but the second half of Season 4 has Nate and Serena rekindling their flame. They totally planned those matching patterns.