From the Valley to the Upper East Side: Lily Van der Woodsen’s Style Cross-Over (1.06 –> 1.11)

I’m spending my Christmas holidays at home with my husband and my daughter, relaxing, cooking and enjoying each and every moment with them. At the same time, I’m going through the screencaps of the first season of Gossip Girl, in search of Lily’s scenes. I must admit I didn’t have a clear memory of all her outfits, and some of them are stunning. I’ve also noticed there’s a change in her style in the different seasons: it’s formal but relaxed with bohemian touches in the first season, it’s girly and precious in the second (lots of amazing jewellery) and a little more formal in the third.

But let’s start from where I stopped last time, from The Handmaiden’s Tale [1], the sixth episode of the first season. In this episode, Lily appears only twice: the first time she is in her apartment with Serena and is showing her the dress she’ll wear that night, for a party at the Waldorfs. The Moroccan-themed party will not be the only party of the night, since the younger set will attend a masquerade ball.

Lily is wearing a simple black t-shirt dress, with her hair loose and tiny diamond stud earrings as accessories.

She goes to the party with Rufus, with the apparent intention to make Bart Bass jealous, but something is going on bewteen them. I love her outfit here, so chic and age appropriate.

She wears a Matthew Williamson kaftan dress, made of dark chocolate chiffon, with embroideries on the neckline and at the bottom. She pairs it with gold cage sandals and gold filigree earrings.

Her hairstyle is beyond gorgeous: her trademark bun is embellished with braids. This is a refined yet bohemian hairstyle, and Lily will sport it in several occasions (in the third season, too).

Victor Victrola [2] is a very interesting episode: it closes with the steamy limo sex scene between Blair and Chuck, and it revolves around Chuck’s first attempt to follow his father’s steps as enterpreneur. Lily appears in several scenes, but she only sports two outfits. The first scene is set in Bart’s office, where he’s telling Lily he wants to go public with their love. In this case, she wears a dark outfit.

We know she loves pussy-bow blouses, and in this scene she’s wearing one, made of dark chocolate satin. She wears it with tailored black trousers.

Lily loves important accessories, but her choices are always classic, like the gorgeous Chanel 2.55 flap bag she totes in this scene. The red of the bag is a nice flash of colour in an otherwise dull-coloured outfit.

The second outfit is much more casual. Lily first sports it while meeting Chuck in the courtyard of the Palace Hotel. He’s devastated because his father doesn’t allow him to invest on the Victrola, an old-time burlesque club, and Lily tries to comfort him.

She wears a metallic beige trench coat, skinny jeans and a plain v-neck grey t-shirt. The classy touch is given by a Hermès watch, the Cape Cod, with the leather strap in Orange Potiron. I love the colour of the watch-strap, but I also love the fact that it wraps twice around the wrist, like many other Hermès accessories. She also carries a Valentino Signature metallic gold bag, which matches the colour of the trench.

She sports the same outfit when she goes to Rufus’ art gallery. The trench coat she’s wearing is belted, has gold buttons and is a Tory Burch creation.

Blair Waldorf Must Pie [3] is one of my favourite episodes: it is set on Thanksgiving and it’s full of drama, centred on the tension between Lily, Rufus and Alison, Dan and Jenny’s mother who has returned home. We are also given a glimpse of Serena’s old wild ways, with flashbacks from the Thanksgiving of the year before.

In the first scene, Lily and her children are strolling in a street market, when they speak about their plans for the day.

Lily would like to buy a pumpkin and cook the traditional pie (the same pie Blair is so fond of), but she desists: after all, she’s a socialite, not a housewife.

The outfit she wears in this scene is pure perfection because it’s simple and timeless. She pairs skinny jeans and a plain long-sleeved t-shirt with a black long jacket and black ballerina flats. Her accessories represent another Hermès moment: she carries her Kelly bag and wears a lovely white and black printed silk scarf around her neck.

When they get home, Serena and Eric receive an invitation from Dan for lunch. Lily is leaning on her couch and reading a book: for this reason, she’s wearing a chocolate cashmere hooded robe, a perfect piece of loungewear. Serena eventually convinces Lily to go with them to Brooklyn.

When they step into the Humphreys’ loft, the atmosphere is chilly, since Alison knows Lily was Rufus’ first love. In this screenshot, we can see Lily in full figure: she’s wearing grey flared trousers and a military black coat.

The cut-out blouse she’s wearing under the coat is one of the most beautiful garments I’ve ever seen on Gossip Girl. It’s romantic without being frilly, it gives her an amazing light and softness. As for her accessory, she wears a gorgeous Hermès watch, the Medor, the most beautiful Hermès watch ever. The dial is hidden under the stud at the centre.

As I have written a few lines above, there are some flashbacks from 2006, when Lily and Eric go to the Waldorfs to pick a dizzy S up. In this scene, Lily is wearing another pussy-bow blouse, with black embroideries on the cuffs and on the neckline, and black trousers.

The main event of Hi, Society [4] is a debutante ball, which involves all the characters. This is the first time we meet Lily’s mother, Cece, who has been the chairwoman of the event for a long time, now followed by her daughter, who is now in the committee.

In the first scene, she’s following the preparations for the ball. Her outfit is simply stunning: she wears a grey cashmere sweater dress and an enviable number of Hermès accessories. If I think about all the Hermès moments Lily has given us, this is the best by far.

Her Medor watch is followed by gold stud earrings and an astonishing belt, the iconic Collier de Chien. She also carries her trusty Birkin bag in ostrich leather on her arm. I think the cashmere pashmina wrap hanging from her bag is by Hermès, too. I love the shades of these accessories, all warm brown tones, perfect for Lily’s blonde hair and fair skin.

At the end of the day, Cece, Lily and Serena enjoy some time together, sipping a tea in the living room of their apartment. In this case, Lily wears a simple brown satin robe; the same garment, in different colours, is worn by the other characters.

Jenny is so eager to be part of the Upper East Side world, that she lies to Lily, telling her she can help out for the ball (while her parents don’t want her to). Tension can be felt when Lily and Jenny meet Alison while shopping for a ball dress at Saks Fifth Avenue. The suspended glass balls make the shoe department a sort of fairy land, and are the ideal set for the crash of Jenny’s dreams. In this scene, Lily wears a sleeveless beige sheath dress and has her Medor watch at the wrist.

At the ball, Lily wears a black halter gown, with a plunging neckline. This dress is so sexy and refined! She is also wearing a white gold and pearl lariat necklace and a shoulder bag made of exotic leather. I love her hairstyle, because it’s a romantic version of her trademark bun.

The last episode of this post is Roman Holiday [5], the Christmas episode of the first season. Lily’s style is at her best: she sports three outfits, all equally representing different aspects of her complex personality.

Lily and Bart go to the Constance Billard and St. Judes schools to attend the Christmas party, and there they meet Rufus and Alison. Lily wears a beige turtleneck sweater and a trench coat, and she carries a black bag.

Her trench is a classic Burberry piece, with gold buttons, and her bag is a Hermès Trim, a bag Kelly Rutherford owns in real life.

Later that day, Lily and Bart attend a holiday party at the Waldorfs. She receives a phone call from Rufus, who has discovered Alison’s lover wants her back and she wants it too. Rufus wants Lily, but she cannot take a decision yet.

At the party she wears a gold dress by Collette Dinnigan, with lace on the neckline and on the bodice, and sequin embroideries all over the skirt. This is not a typical Lily look, but she looks flawless as usual. I usually don’t like white, yellow or gold clothes on blondes, but this dress really suits her.

The final scene takes place at the Van der Woodsens’ apartment: Lily, Bart and their children gather around the Christmas tree to unwrap their presents. In the first screencap, Lily is wearing a brown shirt dress and is holding a red jewellery box (Cartier!) in her hands. The content of that lovely box is unsaid, but never mind, because Bart’s present – a breathless diamond engagement ring – is fully displayed and leave us longing for more eye candy. In the second screenshot, Lily’s necklace can be seen, made of glazed gold oval links.

More posts about Lily’s style in the first season are coming, so be sure to check back soon!

[1] This title is a reference to Margaret Atwood’s The Handmaid’s Tale, a feminist dystopian novel published in 1985. Five years later, the German director Volker Schlöndorff made it into a movie, starring Natasha Richardson, Aidan Quinn and Faye Dunaway.

[2] Victor Victrola clearly refers to Blake Edward’s Victor Victoria (1982), a disguise movie starring Julie Andrews in the role of “a woman pretending to be a man pretending to be a woman”.

[3] I’m not sure of the primary source of inspiration for the title of this episode: my first choice is Romeo Must Die (2000), an action movie by Andrzej Bartkowiak, starring Jet Li and Aaliyah. The second choice is John Tucker Must Die (2006) by Betty Thomas, a college comedy starring Jesse Metcalfe and Brittany Snow.

[4] I love when Gossip Girl episode titles are inspired to Old Hollywood movies: this is the case of Hi, Society, inspired to High Society (1956) by Charles Walters, a lovely musical comedy starring Grace Kelly, Frank Sinatra and Bing Crosby.

[5] What I’ve written in the previous note is true for Roman Holiday, too, because it is exactly the title of the cult-movie by William Wyler (1953), starring a gorgeous Audrey Hepburn (Blair’s favourite actress) and Gregory Peck. Talking of Blair’s passion for Hepburn, she refers to her movies in several occasions and in the starting scene of The Blair Witch Project (1.14), she re-enacts the closing, under-the-rain scene of Breakfast at Tiffany’s.

Source and source.




  1. ciao superqueen, oggi ho pensato a te perchè sono andata a vedere una grande mostra di abiti da sera di Mila Schon a Trieste, abiti dagli anni Sessanta agli anni Novanta, con superbi lavori di paillettes, applicate con una maestria come non ne ho mai vista. Pigiami palazzo e abiti bizantineggianti, una serie di abiti ispirati a Persepoli, e altri abiti bianchi e neri ispirati alla skyline di New York…. che meraviglia. Hai visto il libro appena uscito, “Il cacciatore di Birkin”? l’ho comprato e letto, è interessantissimo: te lo dico perchè vedo che in questo post si parla di Hermés (che a me tra l’altro non dice molto…) auguri cari di Buon Anno a te, all’ingegnere e a Miss B. ! Ombraserena.

  2. Ciao!
    Mila Schon è un nome che mi ricorda la mia infanzia, quando i suoi abiti comparivano su Vogue Italia, assieme a quelli di molti altri designer che ormai non ci sono più. La mostra deve essere proprio interessante!

    Purtroppo no, non ho ancora avuto modo di dare un’occhiata al libro di cui parli, ma la prima volta che capiterò in libreria, lo cercherò, mi è venuta la curiosità di leggerlo.

  3. Lily is carrying a Valentino Signature bag in the V/V scene with Chuck.

    And in the Hi Society scene at Saks her brown quilted bag is Chanel (but it is difficult to get a clear pic of it).

  4. I would like to call the people who buy the clothes for Lily’s character on the tv show and tell them, every time you buy anything for Lily, just pick up a second one for me, too, please : )

  5. my husband and i watch gossip girl together and he loves lilly’s style on me because of my frame but he steers me away from dark colors when we shop for my clothes because he says it makes me look pale. I have dark brown hair and tan and not very good with picking the right color for my skin tone. he, on the other hand, does a great job doing that but i also want to be able to pick my own clothes. any guidelines?

    1. Well, it depends on your tastes. I am brunette with a medium complexion (NC30, according to MAC system) and I love wearing clothes in dark colours, especially black and grey, because I think they are always refined. I also like neutrals, but I rarely use them in my outfits because I think THEY make me pale. I love bright colours, as well, in particular red. I try to use pastel colours with care, I hate looking like a doll. Try to experiment with colours and never stick to the safer option!

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