From the Valley to the Upper East Side: Lily Van Der Woodsen’s Style Cross-Over (Pilot –> 1.05)

Are you feeling lost without Gossip Girl as much as I do? I’ve recently read that the next episode will be aired at the beginning of March 2010, and just thinking of all this time without my favourite tv show makes me feel so sad. During these Christmas holidays I’d like to watch some episodes of the first two seasons again, but in the meantime I’ve decided to get back to the beginning: as you may remember, some months ago I wrote two short posts about Lily Van der Woodsen’s style in the first and second season, but now the series has temporarily stopped, I can write something more about it.

The first time the character of Lily is introduced, she’s taking part into a posh party at the Waldorfs. Serena gets back from her Swiss seclusion and immediately reaches her mother at the party.

The socialite and classy side of her personality is emphasized by the outfit she sports in the first scene, where she’s wearing a lovely black dress with a deep neckline; the jewellery she wears is precious but understated (a gold necklace with diamond pendant and small diamond earrings). Her hair is styled into a bun and side-parted.


Van der Woodsen’s family drama is based on Eric’s recent suicide attempt. Serena and her mother soon meet at the hospital where Eric is staying.

Even if she’s not attending a party, Lily’s style is flawless: for a day outfit, she prefers neutral and warm shades, which beautifully complement her blonde hair and fair complexion. In this scene, she’s wearing a short-sleeved cashmere sweater and a brown scarf. A bag – a Hermès Birkin bag, for sure – can be half seen in the first screenshot.

In the pilot Lily meets the true love of her life, Rufus Humphrey, who is running an art gallery (the Bedford Avenue gallery, in Williamsburg). The two seem to meet by chance, but we all know Lily still has feelings for Rufus.

Lily’s outfit here is completely different from what we’ve seen so far. This one shows her relaxed and bohemian side: she is wearing a metallic bronze trench coat (the first of many trench coats she’ll wear in the first season), a simple tee and flared jeans. She completes the outfit with a knitted scarf, black sunglasses and one of her Hermès Birkin bags (this one is made of ostrich leather). Her hair is styled in a messy bun and side parted.

The second episode, The Wild Brunch [1], opens with all the characters getting ready for a brunch, hosted by Chuck’s father to benefit his charity foundation. The first scene where Lily appears is set at the Palace Hotel, where Lily and Serena are living (their apartment is being renovated).

Lily is wearing loungewear – a brown satin dress and a matching long-sleeved wrap. She loves wearing cozy and warm garments when’s she’s at home.

In the following scene, she’s back to her formal style: she’s talking to Nate and wearing a Dolce & Gabbana white brocade short-sleeved jacket and a black skirt. Her bag immediately focuses the attention, because it’s one of the best she’s ever sported, her trusty Hermès Kelly bag in black Barenia leather with gold hardware. This bag is part of Kelly Rutherford’s personal collection and perfectly completes this outfit.

During the episode, Lily and Rufus meet again. This is one of the few times she’s wearing sunglasses: she’s chosen a classic style, Oliver Peoples Harlot sunglasses in white. In the first screenshot above, we can get a glimpse of Hermès Medor watch around her wrist.

In a rare full-figure shot, we can have a better view of this outfit. In this case, she’s talking to Bart Bass in the courtyard of the Palace Hotel (Dan is overhearing the conversation and discovers their secret affair).

She is not wearing the white brocade jacket, so the attention is on the blouse with the jeweled neckline by Robert Rodriguez. She’s also wearing a black pencil skirt and black pumps.

Poison Ivy [2] is all centred on the Ivy week at school, as everyone is stressed about getting into the college of their dreams. Serena is more concerned about her brother, so she asks her mother for a meeting at the hospital.

Lily doesn’t agree with Serena’s desire to take Eric out of the hospital, but she eventually allows him to take part into the Ivy party. In this occasion, Lily is wearing a casual outfit – a dark grey sweater, black trousers and black pumps.

She also wears tiny stud earrings (the only jewellery in this outfit) and a masculine stainless steel watch. I love this tough touch in a very cozy and feminine ensemble.

At the party, Blair’s plot against Serena reveals Eric’s suicide attempt. In this case, Lily is wearing a very formal outfit – a black pencil skirt, a grey top and a black jacket; the accessories are formal as well – pearl necklaces and a Chanel bag. I haven’t found pics where the bag is well visible, but it reminds me of the Diamond Stitch line.

In Bad News Blair, Lily appears only once, when she goes to Rufus’ gallery. She has bought a painting by Rufus’ wife through her art dealer, but when she comes to know who the artist is, she returns it.

In this scene, Lily is wearing a black tuxedo jacket and trousers, with a ruffled blouse, a very simple but chic outfit.

She is carrying a frame bag with a chain handle. The chain shape reminds me of Roger Vivier’s bags, but I haven’t found a decent close-up of the bag to be sure. I usually prefer Lily’s hair in an updo, but she looks lovely here with her hair side parted and let loose.

Dare Devil [3] is one of my favourite episodes, because it’s full of tension and events – Dan and Serena’s first date, Eric’s escape from the hospital, the traditional sleep-over at Blair’s, Jenny’s desire to be part of Blair’s Mean Girls.

The first scene in which Lily is present is set at the hospital, where she goes to visit Eric. Here she sports for the first time a staple of her wardrobe, the pussy bow blouse. She wears an emerald green satin blouse with a beige tailored jacket and black trousers. She also carries a dark red shiny crocodile bag.

While she’s leaving Eric’s room, her belt is visible and the big H screams Hermès again. This is the iconic Constance belt, with the capital letter H in gold metal. I usually don’t like monogrammed items, but this one is truly a classic, and is perfect in Lily’s outfit.

In this episode, we are lucky enough to get another Hermès moment. When she receives a phone call from the hospital, announcing Eric has left, she goes to Rufus, hoping her son is with Serena and Dan. Here she’s wearing a black leather jacket and totes her Birkin bag in ostrich leather.

I’m in love with her leather jacket, which is has quilted inserts on the shoulders and on the front.

This is a Zara item, but I guess it is inspired to Burberry Prorsum fall/winter 2007 collection.

At first Lily is furious with Rufus, because she thinks he may be responsible for hiding the truth about Eric’s escapade; then, when the events become clearer, she stops at the loft and cooks the dinner with him. This familiar moment between them is so romantic.

In this scene, she has taken her jacket off and wears a simple James Perse v-neck grey tee. I like her wing-shaped silver pendant hanging from her necklace. She also gives us another Hermès moment, because she’s wearing a Constance reversible belt with gold buckle.

In one of the latest scenes of the episode, Lily is ready to go to bed and speaks to Rufus on the phone. This is the first time we see her in her nightwear. In this case, she’s wearing a black night-dress with scalloped embroideries on the neckline, très chic.

I will write more about Lily’s style in the first season, so get back soon.

[1] The title of the episode is inspired to The Wild Bunch (1969) by Sam Peckinpah, a western movie set just before World War I.

[2] The title can be referred to Batman’s enemy, the eco-terrorist Poison Ivy, or to the protagonist of the 1992 movie of the same name, a seductive teen played by Drew Barrymore.

[3] The title refers to the movie by Mark Steven Johnson, starring Ben Affleck, Jennifer Garner and Colin Farrell, based on the superhero created by Stan Lee for Marvel Comics.

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13 comments

  1. Thanks so much for this! I love reading your blog each week on Lily’s style. I was sooo sad when I learned we weren’t going to get an episode for three months because I’m so used to coming here and learning about her fashion!! I’m also totally in love with Lily’s quilted leather jacket as well! I’ve been looking for something similar for a looooong time!

  2. This long winter hiatus is so frustrating, because the last two episodes were really juicy and now I’m so looking forward to see what will happen next.

    In any case, I’ll write more posts about Lily’s style in the first and second season. I hope you’ll enjoy them 🙂

      1. Thanks a lot! It is stunning to notice the resemblance of this jacket with the one by Burberry, even the (misleading) shape of the buttons is the same.

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