The 10 Most Enviable ‘Gossip Girl’ Outfits Of All Time

“Destiny is for losers. It’s just a stupid excuse to wait for things to happen instead of making them happen.”

Blair Waldorf might be a bit harsh, but no one can deny that she is stylish.Whether you love Gossip Girl or hate it, you have to admit that the fashion from the show is bold, unique, and some might even say iconic. From Blair Waldorf’s signature headbands to Lily Van Der Wooden’s everything, the varying textures, colors, and styles are never boring. The following includes a list of only the best of the best looks from Gossip Girl.

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1. Anything With Audrey

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For those of you whom are unfamiliar with Gossip Girl or Audrey Hepburn, know that Blair Waldorf idolizes classic, old Hollywood glamour. In many of Blair Waldorf’s dream scenes, modernized versions of Hepburn classics are depicted, such as Breakfast at Tiffany’s, My Fair Lady and even Wait Until Dark. Blair’s classic khaki trench coat and little black dress are staple wardrobe necessities. It must be emphasized that the sophisticated and evidently timeless Audrey Hepburn first donned them herself.

2. The White Party

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Although they prohibit you from drinking red wine, white party attire is all the rage. Everything looks clean, crisp and almost angelic—a difficult feat for plenty of Upper East Sider sinners on the show (*cough* Chuck Bass). Nate looks especially dashing in white pants and an off-white grandpa cardigan. Serena dazzles us in a goddess-esque, white maxi dress. Blair looks spectacular in a white bandage dress, donning a flower headband to top off the look. With a tuxedo lined in black and a sexy black ascot, Chuck Bass is winner of the white party apparel look.

3. Serena’s Parisian Look

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A rose-gold, sparkly cage dress contraption? Yes please! Complete with ballerina pink oxford shoes, a gray blazer and classic fedora, Serena’s look is work meets play. It is sophisticated enough for a meeting but flirty enough for a night on the town. The outfit has a cool combination of feminine sparkles and lace, with the preppy oxfords and blazer. On many girls, this outfit would appear too outrageous, but for Serena Van Der Woodsen, it absolutely works.

4. Blair Waldorf in Alexis Mabille

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Not many people can pull off something as elaborate as a dress that has flowers, sparkles, gold, pastel and black all in one outfit. Looking like royalty, Blair wears this dress with ease—even when she is threatened by a business man and crashing a thirteen year old’s bar mitzvah. The elevated shoulders give the appearance of power and the delicate tulle flowers lend an air of feminine worldliness. Can I also have her matching bedroom please (just kidding…kind of)?

5. Serena’s Sweater & Skirt Outfit

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A neutral-toned, knit sweater tucked into a bohemian skirt never looked so good. Serena rocks a more laid-back outfit, complete with classic black tights and a statement necklace. Even though Gossip Girl features a plethora of expensive designer dresses, purses —you name it— this outfit is more low-key. It seems like something you could easily find at your local Urban Outfitters or even Target, and that is why I love it. Most sweaters tend to look lumpy or matronly, but this short-sleeved, cozy sweater with youthful cutouts is quite trendy.

6. Lily Van Der Woodsen’s Anything

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Every outfit that Lily Van Der Woodsen wears is flawless, especially this long-sleeved black dress with a Christian Dior clutch. From the subtle sparkles on the dress shoulders, to Lily’s always perfectly coiffed updos, Mrs. Van Der Woodsen is a queen. She wears jewelry to look elegant and classy without seeming overly extravagant or excessive. Moreover, even in chaotic times, Mrs. Van Der Woodsen always looks poised and put together.

7. Chuck Bass in blue

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Only Chuck Bass can pull off paisley with pinstripes in pastel and navy hues. Throughout Gossip Girl, his style has evolved from his signature scarf and colorful ridiculousness to sharp, sexy business suits—with a one-time appearance of a random, red onesie and Nike sneakers. Nothing screams power like a solid pants suit and a Chuck Bass grin, am I right? As Blair would say, “Damn that Mother Chucker!”

8. Eleanor Waldorf designs!

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Who can forget when Blair and Serena had their own photo shoot, with all of Manhattan as their backdrop? The blue and coral silk dresses are classic and classy, tailored just above the knee, with quarter-length sleeves. Metallic, nude heels and kissy faces are the piece de resistance for this look. The duo also snapped a picture of themselves with a digital camera. O.G. selfie anyone? Perhaps these outfits are the ultimate best because “Serena and Blair, they do besties better than anyone,” and because the most important accessory anyone can wear is a smile.

9. Serena Van Der Woodsen in Georges Chakra wedding dress

GOSSIP GIRL-- 'New York, I Love You XOXO' -- image GO610C_0105 Pictured (L-R): Taylor Momsen as Jenny Humphrey, Connor Paolo as Eric Van Der Woodsen, Blake Lively as Serena Van Der Woodsen and Penn Badgley as Dan Humphrey -- Photo: Giovanni Rufino/The CW -- © 2012 The CW Network. All Rights Reserved

Gossip Girl features an abundance of wedding dresses due to all of the nuptials that occur throughout the series, but no one can deny that Serena’s dress is one of the best. Giving the illusion of spilled paint, the Georges Chakra gown is draped in dripping gold. As she waltzes down the staircase to the collective harmonies of Florence and the Machine (fun fact: Blake Lively & Florence Welch are besties IRL), Serena Van Der Woodsen is the picture of absolute grace and gorgeousness.

10. Blair Waldorf in Elie Saab wedding dress

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If I had to pick only one outfit from all six seasons of Gossip Girl, this is it. Gossip Girl’s costume designer Eric Daman describes how the dress, “needed to feel like old world glamour meets contemporary high fashion.” The lacy, bead-encrusted dress is exactly that. The sheer, nude fabric layered with intricate, diamond-covered flowers is flirty, feminine and quite Gatsby-esque. Accessorized with turquoise drop-earrings and a Blair Waldorf signature diamond leaf headband, Blair’s outfit is true perfection. The final touch is when Chuck Bass says those three words, eight letters—I love you.


 

Who am I? That’s a secret I’ll never tell. You know you love me! XOXO

-Gossip Girl.

Tiffanie Snyder

My name is Tiffanie Snyder! Studying Media, Culture, and Communications (MCC) at NYU as a twentysomething, I spend my time immersing myself in any kind of movie, book, or magazine I can find. Chai tea is my beverage of choice, and I love almost all food. I have a Pomeranian named Tackle. Join me on my roadtrip down Twentysomething lane.

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