From the Valley to the Upper East Side: Lily Van der Woodsen’s Style Cross-Over (2.04 –> 2.09)

It’s been awhile since I last posted about Lily Van der Woodsen’s outfits in Gossip Girl, so here I am. This time, I have written about the second season, from the fourth to the ninth episode. As you may have noticed, a change in Lily’s style is very clear: the basic and understated looks she sported in most of the first season, will slowly recede, giving way to more feminine outfits, with bright colours, ruffles and flower prints. Her love for jewellery will take a new direction, because she will wear more and more precious items, culminating in a true obsession for Van Cleef & Arpels. I actually miss some of the outfits of the first season, because they perfectly matched Lily’s complex story and personality. Now, in the second season, it is as if her wild and bohemian side gives way to her self driven by social conventions and responsibilities.

The Ex Files [1] opens with Lily and Serena having breakfast together. Lily has just come back from her honeymoon, Bart is in Beijing for a business trip and she is probably starting regretting her decision to marry him.

We often see Lily in her sleepwear and she’s impeccable as when she wears daywear: in this case, she’s wearing lavender satin slip and robe. The slip’s neckline is trimmed by black lace.

Lily is now married, but she cannot avoid going to Rufus’ gallery to pay him a visit.

This is one of the best outfits seen on Lily, because it’s classy and fresh at the same time: she’s supposedly wearing skinny jeans with a Stella McCartney floral chiffon top, with flutter short-sleeves. Here we get the first Hermès moment of the second season, because she carries her Kelly bag in Parchemin, a gorgeous neutral beige colour. This bag is part of Kelly’s personal collection.

Lily’s passion for Van Cleef & Arpels jewellery is not a secret, so it’s not a surprise to see her wearing a long necklace and earrings in white gold and turquoise from the Alhambra Vintage collection.

Later, at Rufus’ loft, she would like to rekindle their love story, but he reminds her she is now Mrs Bass and has to live with it. He tries to go over the delusion and starts dating a girl.

Flutter sleeves seem to be the style leit motif of this episode. At Rufus’ loft she is wearing a black blouse with flutter sleeves and a lace insert on the front.

She has kept accessories simple, wearing diamond stud earrings and a black Deco bangle by CC Skye.

The Serena Also Rises [2] is an episode full of drama, not only because of the on-again-off-again feud between Serena and Blair, but because a new subplot about Lily’s past surfaces. In this episode, Lily is busy with decorating her new apartment, which she fills with interesting art pieces. Take the infamous “Prada Marfa” sign, created by the Scandinavian artists Michael Elmgreen and Ingar Dragset in 2005: it is related to their brilliant permanent art installation (a Prada shop) in the desert of Marfa, a tiny town in Texas.

This summery outfit is very much Lily in the second season. She pairs a Rebecca Taylor purple satin blouse (flutter/ruffled sleeves again!) with an Elie Tahari Leila patterned skirt.

To complete the outfit with a matchy-matchy accessory, she chose a Gabriela de la Vega Maryjane cluster necklace in lavender chalcedony.

Later in the episode, while Lily is having lunch with Serena and her socialite friend Poppy Lifton, we get a glimpse of her complete outfit: she’s wearing Christian Louboutin Simple pumps in cream leather.

Talking about summery outfits, here it comes another one. I love this Brooke dress by Kate Spade, because it has a basic shape with a beautiful floral print. Kelly’s enviable figure is emphasized in this dress, which shows some legs.

The gorgeous necklace she’s wearing is a creation by Rachel Leigh: this Millie’s Eating Contest bib necklace is made of gold-plated metal with resin beads and cabochon. The colour combination of the necklace on Lily is Pacific.

When it comes to Bart and Lily, things are complicated: he has discovered she posed nude for Robert Mapplethorpe and he buys the portrait because he thinks this might be incriminating for his career; at the same time, he has hired a detective to dig in Lily’s past. Lily is shocked but she cannot react when Bart proves he has actually found something incriminating in her past (we can assume he knew about Rufus and Lily’s son).

When they meet in Lily’s living-room, she is wearing a Nicole Miller purple satin dress with square neckline and puffy cap-sleeves.

Bart is a dark and conspiring character, but he surely knows how to make a woman happy. Look at Lily’s face when she sees her husband’s most recent gift, a stunning diamond and emerald necklace. Wouldn’t you be as much surprised, if you were her?

In New Haven Can Wait [3] the feud between S and B explodes, culminating in a cat-fight at the dean’s party in Yale. Lily appears in the first scene, when she goes to Serena’s bedroom.

She’s wearing a black and white sleeveless dress, with gatherings on the neckline and a belt at the waist. I really like this dress, because it’s simple and chic. Lily doesn’t add important accessories and lets her hair loose.

Later in the episode, when all the main characters are in Yale, Lily goes to Serena’s bedroom (which will become Jenny’s bedroom in the third season) and tries one of her bodycon dresses on (designed and crafted by Jenny), just to see how it looks on her. This is not Lily’s style, but you must agree she looks stunning.

This dress has got a plunging neckline and bold shoulders, very much Serena. Lily wears it with her Louboutin Simple cream pumps.

We get another glimpse of the dress the following morning, when Lily hangs it in Serena’s closet. In this scene, she’s wearing a dove grey satin shift dress with abstract prints and flat thong sandals.

Chuck in Real Life [4] is full of drama, because of Serena’s rebellious behaviour against Lily and her husband. Bart is worried because he thinks Serena’s overexposition on the gossip press can be a problem for his career.

In a scene where Lily confronts her daughter, she’s wearing a black dress and a gorgeous turquoise and gold beaded necklace and matching bracelet. I love how this colour compliments her fair complexion and blonde hair.

The dress is a Robert Rodriguez creation: it is made of black silk and has interesting petal-shaped sleeves.

There are lots of guests and journalists at Lily and Bart’s house-warming party. Lily looks lovely and she does what she can to counterbalance the tension Serena (who will eventually sabotage the party) is building against her and Bart.

For the big event, she chooses a red Giorgio Armani dress, with spaghetti straps, balloon-shaped skirt and bodice with a folded decoration. I don’t like this outfit, because I think the shape and the colour (orange-based red) of the dress don’t suit her much.

I don’t like the hairstyle either, because this slightly pouffant updo makes her look older than her age. Luckily, her jewellery is to die for: she wore a gold bangle and a pair of Van Cleef & Arpels Cosmos flower-shaped earrings in white gold, ruby and diamonds.

It’s very rare to get a full-figure of Kelly Rutherford in the show, and this is so much true in the second season, because at the time she was pregnant with Helena. From the shot above, her shoes are visible and from the puffy feather decorations on the front, I think it’s quite safe to assume she was wearing Christian Louboutin Rosazissimo satin sandals.

The day following the party, Lily wears a conservative outfit – a black cardigan over a black dress – made special by a stunning diamond necklace and matching drop earrings.

There Might Be Blood [5] brings drama in Rufus’ family, when Jenny – who has already left school for pursuing her dream of being a designer – decides to crash the New York Philanthropist Society’s annual gala (honouring Bart and Lily)  with a guerrilla fashion show.  We can only see Lily in the scenes of the gala.

The first thing that caught my attention is Lily’s hairstyle and jewellery. Her trademark updo is more modern thanks to a wavy styling and a braid, lovely! As for the jewellery, she wears an intricately ornated gold filigree necklace, with an oval pendant, matching earrings and bracelet. I am not crazy about this choice, because there seem to be a jewellery overload: the necklace is an important piece and it would have been enough.

Her dress is a Vera Wang Lavender Label creation: it is made of navy silk taffeta, with cap-sleeves and a plunging neckline. Lily pairs it with her trusty Louboutin Simple pumps.

We can see another Lily’s outfit in an official portrait of the couple, shot for the gala.

In this case, Lily is sporting the same weavy updo as before and she’s wearing a gorgeous Vera Wang one-shouldered black dress, with a ruffled decoration on the shoulder and a ribbon belt at the waist. Too bad a full-shot is nowhere to be found, because she looks really beautiful.

More outfits from the second season are about to come, so check back soon!

[1] The title of this episode refers to the famous series by Chris Carter, The X Files, aired from 1993 to 2002, starring David Duchovny and Gillian Anderson.

[2] I’m sure that Ernest Hemingway would be happy of this homage, if he were alive: the title of the episode is inspired to one of his most famous novels, The Sun Also Rises (1926), about a group of expatriate Americans living across France and Spain, where the protagonist, Jake Barnes, attends the famous San Fermin festival.

[3] The title is a reference to Heaven Can Wait (1979) by Warren Beatty and Buck Henry, a comedy starring Warren Beatty and Julie Christie.

[4] Dan in Real Life (2007) by Peter Hedges, a comedy starring Steve Carell and Juliette Binoche, is the source of inspiration of this title.

[5] There Will Be Blood (2007) by Paul Thomas Anderson, starring Daniel Day-Lewis, is the movie which served as an inspiration for this episode’s title.

Source and source.




  1. I usually love her hairstyles, mainly her side-chignon, with a messy touch and the braided updo she sported in the sixth episode of the first season. I love her bohemian side, when she’s classic but, willing take risks, stands out.
    Honestly i don’t like the red tulip gown of 2¤7 and the poofy hairstyle.

  2. I was gonna post about the Nicole Miller dress but it looks like you already found it 🙂

    I’m so glad we finally have an idea on the dress.

    1. The pleats on the dress made me think of Nicole Miller’s style. In any case, identifying Lily’s clothes is very difficult!!!

  3. hey!
    nice post…
    do you have any idea what brand is the emerald and diamond necklace that bart gives lily on returning from his trip.

    1. I think it’s a Van Cleef & Arpels necklace, because Lily wore many jewellery by that brand in the second season. Plus, the necklace is very much in VC&A style. Unfortunately, I still haven’t found evidence of my guess.

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