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Gossip Girl Fashion Retrospective: Serena van der Woodsen’s Most Iconic Looks

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Gossip girl - Serena van der Woodsen
Photo from Elle.

These are dark times, you guys. After six seasons, “Gossip Girl” is coming to an end. And, okay, maybe it is time to throw in the towel, because any sense of rational plot has been out the window since season three… but still. This is the end of an era.

Gossip Girl’s fashion is as iconic as its beloved characters, so for the next four days, (leading up to the finale – sob!) I’ll be showing you how to steal your favorite character’s most memorable looks.

Starting us off is Serena van der Woodsen, the Upper East Side’s resident bad-girl-gone-good. Played by the gorgeous Blake Lively, Serena is the master of mixing classic pieces with eclectic shapes and textures. Below, we’ll show her evolution from reluctant prep school pariah to the confident, stylish young woman we know and love today. On to the outfits!

Where has she been?

Serena look 1 with brown leather jacket, striped tee, brown satchel, brown belt, gray slouchy boots, black skinnies, and yellow scarf
Jacket, Tee, Jeans, Scarf, Boots, Bag, Belt | Photo: The CW

It’s odd to think that the endlessly mysterious Serena van der Woodsen would return to the city in a conservative leather jacket and classic skinny jeans, but who are we to complain? With all the drama surrounding her return, Serena’s very first outfit gives us a hint that she might not be the crazy, boyfriend-snatching party girl GG makes her out to be. And that’s kind of the moment we all fell in love with her. Girl sure knows how to travel in style.

Make Serena’s premiere look your own by pairing a tan leather jacket with a conservative striped tee. Black skinny jeans and a yellow scarf update this classic look. Accessorize with the basics, like a deep chestnut satchel and a matching belt. Slouchy suede boots complete this polished and casual look.

Prep School Chic

Serena outfit 2 with plaid skirt gray v neck plaid tie sequin vest gold bangles green satchel and brown riding boots
Tee, Skirt, Vest, Tie, Boots, Bag, Bangles | Photo: The CW

Ah, Constance. Did you even have a uniform policy? Though each character managed to add their own personal twist to the prep school dress code, Serena always took things to the next level. Sometimes it worked (I love every single one of her slouchy, sparkly cardigans), and sometimes she looked like she’d just walked out of a Britney Spears video. Either way, her effortless charm was kind of fabulous.

Steal Serena’s blasé boarding school look by pairing a preppy plaid skirt with a slouchy gray v-neck, topping it off with a subtly sequined vest. Very bad-girl-gone-good. Accessorize with classic staples like a bright, structured bag and brown riding boots, adding a touch of sparkle with a pair of gold spiked bangles. Complete the look with a tie, of course. Go full-on Serena and wear it like a necklace, or wrap it around your hair like a headband. I bet even B would be jealous.

The White Party

Serena look 3 with white maxi goddess dress gold hair chain gold gladiator sandals gold bangles gold pearl earrings and sequin clutch
Dress, Hair Necklace, Sandals, Bag, Bangles, Earrings | Photo: The CW

It’s common knowledge that Serena is 100 percent breathtaking 100 percent of the time, especially when she’s all glammed up. But if I had to pick her most stunning formal moment? The white party. Definitely the white party. This outfit captures Serena’s effortless, ethereal beauty perfectly. Honestly, she might as well be a living goddess.

Pretend you’re a member of the Hamptons elite in a curve-hugging, Grecian-inspired maxi dress. Add gold gladiator sandals for an even more goddess-like look. Glam up your hair with gold hair necklace. (Remember when those were all the rage? Pretty sure that was Blake Lively’s fault.) Finally, keep your accessories glittery but classic – a stack of sparkly bangles, a sequined clutch and pearly-gold earrings complete this jaw-dropping look.

Passport to Paris

Serena outfit 4 with gold blazer cobalt capris white tee nude pumps ivory cross body and spike studs
Blazer, Tee, Pants, Pumps, Bag, Cuff, Earrings | Photo: The CW

By season four, Serena abandoned her disheveled schoolgirl wardrobe in favor of a closet full of classic, bold statement pieces. And oh, how we loved every moment of it!

Yes, Serena’s summer in Paris gave us some of her best outfits yet. (Except maybe for this. I can’t get past those pants.) Fashion-wise, Serena had finally come into her own. These days, clean lines and dramatic silhouettes are no problem for her – the girl is a statuesque stunner and she owns every moment of it.

Snag Serena’s bold, gold-embellished look by pairing a sequined blazer with dramatic cobalt pants. Since it’s still Serena we’re dealing with, sport a slouchy white tee under your blazer. Nude pumps and an ivory-tone cross-body bag add polish, while spike earrings and an embellished cuff add high fashion flair.

Your thoughts?

What’s your favorite Serena look? Are you excited for the GG finale? Let’s hear some predictions! Be sure to let me know what you think of the outfits in the comments, I’d love to hear your thoughts!

Posted on on December 14, 2012 / Filed Under: Inspiration / Tags: , , , , ,

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15 Responses to “Gossip Girl Fashion Retrospective: Serena van der Woodsen’s Most Iconic Looks”

  1. 1
    December 14th, 2012 at 9:43 pm

    The dress she wore to the white party is one of my favorite things from GG. So pretty.

  2. 2
    December 14th, 2012 at 9:51 pm

    yes yes yes!!!

  3. 3
    December 14th, 2012 at 10:01 pm

    Wow! These are great :) But as far as her looks in Paris, I actually loved the pink pants, slouchy tank and turquoise necklace! I thought the outfit you chose was a little over-the-top when I first saw it, kind of reminded me of a bizarre superhero costume. But statement-making is very Serena! I’m excited for the rest of this series and for the show finale!

  4. 4
    December 14th, 2012 at 10:09 pm

    @Elyse

    I actually remember watching the Paris episode and seeing the pink pants outfit and LOVING it because I thought it was a maxi skirt… I guess I was just shocked ;). But Serena always looks great. Glad you like!

  5. 5
    December 14th, 2012 at 10:45 pm

    Ahh, so excited for these GG posts! Serena always looks stunning, but I’ll never forget that dress she wore on her first date with Dan, or that gorgeous dove-grey sweater dress she wore to Blair’s 17th birthday party. Call me a sucker for the early seasons… Can’t wait for a post on Queen Blair!

  6. 6
    December 15th, 2012 at 8:55 am

    Just yesterday I was thinkg about SvdW and googling her pictures and apparently you did the same! This must be fate! :-D

  7. 7
    December 15th, 2012 at 11:26 am

    Such a good post! Please do one for Blair. :)

  8. 8
    December 15th, 2012 at 4:31 pm

    Very cute, but I would LOVE to see a Blair post!!

  9. 9
    December 15th, 2012 at 5:37 pm

    I’m so sad that Gossip Girl is coming to an end. It has been my favorite show for the past 4 years and I am going to miss it! I love Serena’s white party dress. She looked like a goddess!

  10. 10
    December 15th, 2012 at 11:47 pm

    I’m going to miss Gossip Girl as well! It was a good show. I’ll just keep watching it on Netflix. I love Serena’s style. It is so unpredictable and trendy! She’s one of my favorite characters!

  11. 11
    December 16th, 2012 at 2:07 am

    Love GG,love Serena’s white party outfit,very chic and glam!

  12. 12
    December 16th, 2012 at 9:57 am

    Glad you guys like!! Look out for Blair on Monday :)

  13. 13
    December 17th, 2012 at 7:04 pm

    Serena was my fav she always had the greatest coats and accessories. It was very boho chic. She was never afriad of trying different textures. I watch it only because I wanted to see what she was wearing.

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