How to Dress Like Serena Van Der Woodsen From Gossip Girl

How to Dress Like Serena Van Der Woodsen From Gossip Girl

How to Dress Like Serena Van Der Woodsen From Gossip Girl

Yes, another post on Gossip Girl fashion. After my post on Blair Waldorf, I realised that a lot of people probably wouldn’t identify with her style what with it being too dressy and stiff-upper-lip kind of sophisticated. So, I’ve decided to write an article dedicated to the style of the show’s other major female character, Serena Van Der Woodsen (played by the gorgeous Blake Lively) who is Blair’s frenemy or “the Sunshine Barbie to [her] Darth Vader” (in Blair’s own words).

I find the whole idea of Serena’s style rather pointless though. I mean, even if she turns up in dreadlocks and hobo clothes, a person who has an unbelievably amazing name like Serena Van Der Woodsen will still be super attractive. It’s only people like me (with a name which is androgynous and would probably stop 25 cheap-looking namesake guys if yelled aloud on the street) who need to pay attention to their style so as to make up for the lack of pretty names.

Anyhow, let’s move on to a little background information on Serena. She is a blonde goddess who lives on the Upper East Side with her über-rich family. Over the last five seasons, she has done more than an average girl like me can EVER even think of doing. This includes sleeping with best friend’s boyfriend, drug overdose, letting a fellow junkie die of drug overdose, trying to seduce her teacher at boarding school, way too many casual hook-ups, wrecking a marriage by having an affair with a married politician and now I have lost track. Let’s just say that Serena is –ahem– a rather colourful character, but personally, I really like her because she’s just so sunny and kind (and also because Blake Lively is
what I’d want to look like in my agla janam).

Just like her personality, Serena’s style can be quite flamboyant. If Blair is inspired by Audrey Hepburn, Serena is more of a Kate Moss fan with lots of modern pieces in her wardrobe and innumerable accessories. Her 70’s-free-spirit-cum-rockstar inspired sense of fashion is a wonderful contrast to Blair’s old school aesthetic. In terms of fashion clichés, her style can be called “boho chic.”

Serena’s look is ultra-luxe and although inspired by the filthy rich New York Upper East Side’s classic pieces, she always manages to spin on some unique twist to her clothes. Some of her outfits are crazy but so is Serena and hence, she carries them off with perfect élan.

The Clothes

Skinny Jeans:

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skinny jeans

These have been in fashion for a few years now and no one wears them with as much style as Serena. She has endless legs and she shows them off wonderfully in skinny jeans of all shades. They are Serena’s wardrobe staple and she’s usually seen dressed in jeans in preference to dresses/skirts, especially in winters.

Well-Cut Jackets:

Dan de Fleurette

If there is one thing that Serena can totally rock, it’s jackets. Biker jackets, long jackets, cropped jackets, leather-studded jackets, chic tailored jackets, tuxedos – you name it and Serena has them. She wears them in all sorts of colours ranging from muted subtle shades like camel, black or grey to bling ones in metallic or bright pops like red or electric blue. I believe that they’re the real secrets to Serena’s “put together” looks because they’re so well-fitting that they just give a perfect finish to even the most average outfits.


embellished jacket

Although Serena does wear dresses sometimes to indulge in her girlie side, they are not overtly feminine like Blair’s. Serena’s dresses will have some unique twist to them. It could be anything ranging from gold-studded hemlines or crazy prints and sequins to menswear-inspired androgynous dress styles. Basically, Serena will never look hoity-toity like Blair in a dress. She’ll look funky and crazy thanks to the unexpected flair of her clothes and her own attitude.

Embellished Tanks:

Serena is not the formal shirt or feminine lace/crochet top kind of person. Part of her unstudied, offbeat style comes from her tank tops that are easy to mix and match with a lot of other things. Serena wears loose, casual tank tops with shorts or skinny jeans and sometimes even tucks them in one of her boho skirts.

Maxi Dresses:

This is a very recent addition to Serena’s wardrobe. Perhaps it was just a result of her temporary move to LA. Maxi dresses look fabulous on Serena what with her height and figure, and also add to her bohemian wardrobe. She has worn them in all sorts of bright, sunny colours in the past few episodes. However, this may not be a staple for her considering she’s now moved back to chilly NYC.

The Accessories:

Serena’s ensemble really comes together with her fashion-forward and unique accessories. These are also what really display the “boho” side to her style and make her style really stand out.



Serena is a boots girl through-and-through. She wears them all the time. She pairs them up with skinny jeans, dresses, even her preppy school uniform (in Seasons 1 & 2). Boots are chic, comfortable and they make each of her outfits look cooler. Serena also sometimes wears animal print or brightly coloured heels to add the funky factor to her looks. In summers, Serena favours sandals over any other kind of shoes. She seldom wears pumps but is a great fan of funky high heels and gladiators. Unlike Blair, she is not averse to wearing flip-flops sometimes.


Serena is your typical jingle-jangle kind of jewellery person. One of her signature accessories are long necklaces. She has lots of them and is normally wearing one or more from her collection. They are usually hitting her navel and to add to her casual style, she layers them. She also wears bangles sometimes and quite a few of them at the same time in order to make a simple outfit like jeans and t-shirt into something more fun. She sometimes also rocks huge signet or cocktail rings in varying degrees of outrageousness.



There is no such thing as too many accessories for Serena. She can look like a really stylish bohemian with her statement scarves tied around her wavy hair. She also sometimes favours hats in extra bright colours or with large brims/feathers. Serena is not too fussy about structured bags either. Although expensive and designer, her bags can range from extra huge carry-it-all hobo monstrosities to small, elegant Chanel chain classics.

The Make-Up and The Hair:


Serena’s fuss-free attitude is evident in her hairstyles too. Unlike Blair’s sophisticated tight curls and ponytails, Serena has messy wavy hair. She usually wears it down and natural without too much extra
effort and even when she ties them up in ponytail, it’s more funky than elegant.


Serena is more experimental than Blair when it comes to make-up. She is not averse to applying thick eyeliner in different shades and her face is usually highlighted. She is also fond of reddish tints on her lips especially for special occasions. I’m not that much of a make-up expert (in impolite terms, I’d call myself a “noob” but let’s keep it all nice and sweet here) and don’t have the foggiest idea about how to achieve her look. I think it’d be wonderful if one of the pretty IMBB make-up gurus creates FOTD-type tutorial for Serena’s look too.

The best part about Serena’s style is that even though it’s non-conformist and slightly funky, if adapted with care and carried off well, it can look mature and effortless. There isn’t much that you require for this kind of fashion. Throw on a pair of skinny jeans, a tank top, a bright well-fitting jacket, boots, a head scarf, and a layered necklace. Then, blow a kiss to your reflection in the mirror. 😉

Image Sources: 1, 2, 3, 4, 5, 6.

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32 thoughts on “How to Dress Like Serena Van Der Woodsen From Gossip Girl

  1. :inlove: :inlove: :inlove: :inlove: :inlove: :inlove: :inlove: :inlove: :inlove: :inlove: :inlove: :waytogo: :waytogo: :waytogo: :waytogo: :waytogo: :waytogo: :waytogo: :waytogo: :waytogo: :waytogo: :waytogo: :waytogo:

  2. Great article 🙂 🙂 ! Usually I’ve only read about Blair and it was a refreshing change to see Serena’s style covered 🙂 🙂 :heart: both of them 🙂 🙂

    1. Yeah, I’ve usually only read Blair-related style articles only (guilty of writing one myself 😛 ) and that’s why decided to go for Serena’s look instead. :toothygrin: 😀

    1. Hahaha! The only possible way to earn money to dress like her would be to loot A Raja and Kanimozhi’s bank lockers. :silly: :silly:

    1. You do? 😯 :woot: I wanna buy something similar too. Somehow, the only long necklaces I can find look way too tacky. 😐

      1. actually the one i have is no so classy either bt i kinda like the look of it.. the knot and all makes it look pretty overall. 😛 It’s not the same bt i will keep a look out for the one she is wearing. :love: :love:

        1. Haha, if it’s overall pretty, then it ought to be fine. 😛 😛 I’m keeping a lookout for Serena type neckpieces too. 😀 😀

    1. :thanks: Yeah, I love her hair too. They just show that she knows how to have fun, even if they’re all tied up in a super-stylish ponytail. :woot: :woot:

  3. Hmmm….So now I’m a Serena+Blair+ ??? style sense girl…because I can’t limit myself to one or two fashion categories…3 or more is what I like. :specs:

    1. Yes, me too. I just don’t think it’s a good idea to limit your wardrobe and style to just one category. It’s good to experiment sometimes. :joker: 😀

  4. u dint show he rpiucs in her taple long maxi dresses..!! and boho type drapes.:P 😛 😛
    i love those :woot: :woot: :woot: :woot:

  5. u dint show her piccs in her staple long maxi dresses..!! and boho type drapes.:P 😛 😛
    i love those :woot: :woot: :woot: :woot:

    nice writeup as always :)) :)) :))

  6. Another superb article Jabberwocky. :yes: I really like your writing style. Its super entertaining. :toothygrin: especially – “It’s only people like me (with a name which is androgynous and would probably stop 25 cheap-looking namesake guys if yelled aloud on the street) who need to pay attention to their style so as to make up for the lack of pretty names” :lol2: :lol2: :lol2: :lol2: Now I’m really curious to know your name. :methinks:
    I find Serena’s style really effortless and charming. But personally I prefer Blair’s prim and proper style… :))
    Thanks for such a great article. Keep writing.. :thumbsup:

    1. Thankee! :toothygrin: I prefer Blair’s style too though in not all its girlish glory.
      And lol @ the name. It’s Navdeep. I’ve never met another girl with the same name, only guys, and some very weird ones. :silly: :silly:

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