From the Valley to the Upper East Side: Top 10 List of My Favourite Lily Van der Woodsen’s Outfits

This year is coming to an end, as it happened to Gossip Girl. Some days have passed since I watched the final episode and I must admit the idea that everything is over, that we won’t see other episodes of the show, makes me feel incredibly sad. This is quite surprising, because the last 3 seasons were so dull and pointless! In any case, the end of any long-running show makes fans feel the same way. No more posts about Lily Van der Woodsen’s style but one, my top 10 list of the outfits I loved the most. It’s been hard to choose ten looks, because no one can deny that she’s been one of the best-dressed fictional characters ever, but I’ve made it. Please feel free to share your own top 10 list (or whatever) in the comments. Are you ready for no. 1?

THEYSHOOTHUMPHREYSDONTTHEY1. They Shoot Humphreys, Don’t They? (season 3, episode 9): talking about this episode, aired in November 2009, feels so strange, doesn’t it? The central event was the Cotillon and Lily looked amazing in her Reem Acra champagne satin dress and statement crystal necklace. I’m not sure if this is really my favourite outfit, but it’s certainly on top of my list.

DAREDEVIL2. Dare Devil (season 1, episode 5): talk about prehistory! I’ve always loved one of the outfits Lily sported in this episode, because it really symbolizes her rock chick roots. Unfortunately this mood got lost in the last seasons, but it’s probably the reason why I fell in love with this character. In the scene above, Lily went to Rufus’s loft to check if Eric was with Dan and Serena (the boy had left the hospital he was staying in): at first she accused Rufus to hide the truth about Eric’s disappearance, but they ended up making dinner together. Here she was wearing a pair of jeans, a James Perse v-neck t-shirt, a reversible Hermès Constance belt and a Zara leather jacket.

ITSAWONDERFULLIE3. It’s a Wonderful Lie (season 2, episode 12): if you are Gossip Girl fans, you can’t forget the night Bart Bass first died. This episode is epic for its hectic plot and for the romantic atmosphere of the Snowflake Ball. I think this is the first time in which we realized that Rufus and Lily were destined to be together. At the ball she wore a gorgeous Vera Wang dress, accessorized with a Musa clutch by Salvatore Ferragamo and a stunning set of jewellery by Van Cleef & Arpels. I cannot help but miss the most luxurious habits of Lily in the first seasons, which included Hermès bags, Van Cleef & Arpels and Verdura jewellery.

SEDERANYTHING4. Seder Anything (season 2, episode 21): this is another of my favourite episodes of the show, because it was full of twists and unexpected turns. The central event was the Passover Seder dinner hosted by Eleonor Waldorf: Rufus and Lily, Serena, her boyfriend Gabriel and even Dan (as a waiter) were in attendance. I love the outfit she sported at the dinner because it matched apparently contrasting colours – purple (her Magaschoni blouse), green (the beautiful Bounkit emerald multi-strand necklace with removable flower brooch), yellow (the lemon quartz earrings by Bounkit), brown (her VBH bag) and beige (the Isabella Oliver Grace coat).

THESIXTEENYEAROLDVIRGIN5. The Sixteen-Year-Old Virgin (season 3, episode 15): this season was strangely appealing, even if things started getting wrong and boring here. The central character was Jenny and her rebellious attitude, clashing against bossy characters like Blair and Chuck. The endless romance between Lily and Rufus was another central theme. In the scene above, they were attending the dedication ceremony of a museum’s wing to Bart Bass. Lily’s outfit included a lovely abstract-print dress by Dries Van Noten and a saffron chain bag by Judith Leiber. I love how the print of her dress was in tune with the event she was attending (the same approach was used in the 6th season in Where the Vile Things Are).

THEEXFILES6. The Ex Files (season 2, episode 4): this is another “prehistoric” episode 😉 Lily and Bart had just come back from their honeymoon in Beijing but she was not happy as she was supposed to be. As a matter of fact, she went to Rufus’s gallery to pay him a visit as soon as she could. In this scene her outfit was flawless, so much in her style, matching the two sides of her fashion personality (rock/bohemian and chic). She was wearing jeans, a flutter-sleeved floral top by Stella McCartney, the Alhambra Vintage necklace by Van Cleef & Arpels and a fabulous Kelly bag in Parchemin from her personal collection of Hermès bags.

NEWYORKILOVEYOUXOXO7. New York, I Love You XOXO (season 6, episode 10): while going through all the posts I wrote about Lily, I realized I couldn’t leave out the pink dress she wore at Serena and Dan’s wedding in the final episode. This lovely Bottega Veneta number was an unusual choice for her, who tended to wear in neutral tones most of the time, but I love it because I think it symbolized the beginning of something new and positive in her life. It’s true the end of the episode was bitter-sweet because Lily and Rufus were not back together, but this wasn’t a bad decision, after all (as I explained here).

WHERETHEVILETHINGSARE8. Where the Vile Things Are (season 6, episode 6): the central themes of the episode was art and drama and Lily gave us both of them. The outfit she sported in the first part of the episode, when she went to a gallery where a charity auction was being organized. The artistic mood can be found in the clothes she wore, which included an abstract-print dress by Emilio Pucci and a Burberry trench coat, paired to neutral accessories (a Miss Dior chain bag in rosewood python and a stunning pair of Roger Vivier Belle Vivier nude pumps). The jewellery was exquisite, too: she wore a Swarovski Majesty Dark ring and RichRocks pave dome earrings.

THEKIDSSTAYINTHEPICTURE9. The Kids Stay in the Picture (season 4, episode 18): I’m convinced the arrival of William Van der Woodsen (Serena and Eric’s father) in the story had a good potential but went kind of wrong. On the other hand, the introduction of other two characters in this episode (Carol, Lily’s sister, and Charlie, her “daughter”) gave us plenty to talk about. I chose the outfit above, which Lily sported at a family photoshoot, because she looked so charming in it. The black Myrtha dress by Roland Mouret is such a classic piece, flawlessly accessorized with black pumps, Ippolita Lollipop two-drop earrings and Henri Bendel Grande Dame pearl ring. Lily’s trademark outfit was given a different vibe thanks to soft Marcel waves.

GASLIT10. Gaslit (season 4, episode 10): the decision to include this outfit in my list was inevitable. It aired in December 2010, but I haven’t been able to identify it yet. Disappointing, right? Despite this “failure”, I still love it so much! It included a camel cape coat, a python bag with lock and chain and Christian Louboutin Miss Tack patent pumps, Lily’s favourite shoes. In this episode Serena was hospitalized after her “suicidal attempt” (but we know she was drugged by the super-creepy Juliet) and Lily was so concerned for her health. It’s sad that the relationship mother-daughter hasn’t been developed better, but I guess it’s never been among the show’s writers’ priorities.

I’d like to write more about my final thoughts on this show, but I don’t want to feel like the old lady who speaks about the same old things all the time, so I think I’ll pass. I’ve shared my top 10 list of Lily’s best oufits, but now it’s your turn! I can’t wait to read your impressions ♥ xoxo



  1. I love almost EVERYTHING Lily’s worn over the years but here are my some of my fave looks,in no particular order:
    1. s4.03 (The Undergraduates) – I love Lily’s uber-refined Park Avenue princess ensemble. The perfect combiination of the summery orange dress and the turquoise accessories is beyond flawless.
    2. s4.06 (Easy J) – I love the coktail ensemble she wears to the Boom Boom Room, especially the luminocity of the Stephen Dweck bead necklace.
    3. s4.13 (Damien Darko) – I adore the sequined jacket she wears at breakfast. Has anyone noticed how unbelievably refined she always looks eating yoghurt.
    4. s4.13 (The Kids Are Not Alright) – How beautiful and sensual does she look in the Luisa Beccaria satin dress. And the pearl necklace, although one would think is too much, is the perfect accessory for the dress.
    5. s3.07 (How to Succeed in Bassness) – One of my ALL time Lily outfits is the DKNY camel suit and python skin Louboutins. I think it perfectly depicts her refined, Blue-blood lifestyle and understatedly elegant character

    1. Thanks for sharing your top 5 list 🙂

      1. I agree: that floral-print dress and turquoise accessories were such a beautiful and elegant match.
      2. The accessories were exquisite but I think the sheath dress was a bit plain. Still a great outfit.
      3. Oh, well: I’m still obsessed with that sequin jacket, one of the items I haven’t been able to identify.
      4. This time I don’t agree. I loved the beautiful pearl tassel necklaces but the dress was just wrong. It’s beautiful in itself but I don’t think it worked on Lily, maybe because of the colour.
      5. I agree on this one, too. Camel suit and Louboutins: such a flawless combination.

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