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11 Best Gossip Girl Looks from the Show’s Designer

Season four of Gossip Girl begins this evening, with Serena and Blair and their outfits taking over gay Paris. Those outfits, like all the ones before them, are the doings of stylist Eric Daman. He previously worked on Sex and the City and has been with Gossip Girl since the pilot — before Blake Lively was, as Daman puts it, “having dinner with Karl Lagerfeld.” On the eve of the premiere, we spoke with Daman about his all-time favorite looks from the series, including Serena’s first outfit, Blair’s prom dress, and Chuck’s memorably purple basketball duds.

Episode: 101. This was the pilot, in which Serena returns to the city after fleeing for a year. Daman Says: “This is the first outfit we ever see Serena in: iconic French striped T-shirt, beat-up brown leather jacket, a little bit of a neck scarf, and those really great skinny jeans and boots. For me, it’s the iconic Serena look. This sort of nonchalant, ‘I’ve been to Europe, I’ve traveled around, I don’t spend too much time on what I put on, but I always look amazing’ look.”
Episode: 104. Nate and Chuck’s boys’ weekend includes, among other less wholesome activities, basketball. Daman Says: “Money and power are always integral to Chuck Bass, so I wanted this look to be no less than an over-the-top Cribs-, MTV-gangsta-inspired moment. It was a lot of fun to take Chuck’s look from UES to LES. People still talk about the sweat bands, the glasses, and the swagger.”
Episode: 110, in which Blair and Serena come out into society (and Blair pretends to lose her virginity to Nate). Daman Says: “This silver brocade gown that Blair wears to her debutante ball was actually the first dress I ever got to design myself for the series. I was given advance notice from the producers that this was coming down the pipeline and it might be nice to design something that was extra special. So in three days we made this gown. [Blair’s] mom Eleanor had supposedly designed it, and Eleanor is based on Carolina Herrera a little bit, so I was doing a little vintage Carolina. But I wanted Blair Waldorf to have this big bow, so I had a giant bow on the shoulder. I really wanted Blair’s dress to be Marie Antoinette–inspired. It’s very muted silver with a very light floral bouquet on top of it, very beautiful and retro.”
Episode: 117. Lily and Bart Bass’s wedding. Daman Says: “The wedding was supposed to be this couture garden wedding. Ralph Lauren sent over this yellow floral dress with black detail that was really perfect. It’s very easy to look like a bridesmaid, walking behind your mom who’s wearing a custom-made Vera Wang dress. But with this dress, I loved that it had these black accents on it so it wasn’t too bridesmaid-y, because it was very modern. And Serena was wearing little black mini-gloves, so that kept it very Serena appropriate.”
Episode: 201. After a long summer in the Hamptons, the gang attends the White Party. Daman Says: “We were doing the white party for this episode, but on TV you’re not allowed to shoot white because it gives people this weird ghost glow, so you usually have to use cream. We got Blake into this really amazing men’s vest, and then we went out to the Hamptons and the outfit wasn’t working. It was all white and we tried to dye it cream, but it was no good. All of a sudden, it’s the morning when we’re supposed to shoot and I’m thinking, What is Blake going to wear to the white party? Totally by chance, there were these two Grecian gowns on the truck, that had come out to the Hamptons with us for just this reason. She fell in love with it and I fell in love with it, and we coupled it with the metallic chain headpiece, and it became this big giant party moment. Everything happens for a reason.”
Episode: 201. In the Hamptons, Chuck and Blair see each other for the first time all summer, both still hung up on the other, but unable to say those three little words. Daman Says: “At a garden dinner party, Chuck is wearing a light green suit with hydrangea and cabbage rose tones in his shirt and tie selection. It was the perfect moment of art direction — he actually matched the set, and when he and Blair have their sad moment in the garden, it was a symphony of greens and flower blossoms. A memorable moment where costumes and sets work seamlessly to create a visual atmosphere.”
Episode: 224. It’s the end of high school, and thus, prom. Daman Says: “This black tulle Marchesa gown was Blair’s moment of being prom queen. We went through about fifteen or twenty gowns before that one came in. I liked the idea that it was black, but also that it had this majestic giant gold peacock on the bottom; I just really felt like it was perfect. So chic, had such a modern-day Audrey Hepburn red-carpet feel. There are just moments when you see something and you’re like, ‘Oh, wow. She’s perfect for that.’ We had to test out tiaras, too, and a tiara can go pretty-pretty princess really quickly. We found this designer on the Upper East Side named Simon Tu and he does these really beautiful handcrafted, like couture tiara pieces.”
Episode: 304. Jenny accompanies Chuck to a movie premiere (co-starring Olivia Burke and Tyra in flapper gear). Daman Says: “In this episode, Jenny is supposed to be making Blair Waldorf jealous, which is not an easy thing to do, because she’s Jenny Humphrey. I wanted to find something that balanced rock and roll and also couture and glamour. Something that stayed true to who Jenny was, and was fabulous enough to get Blair to think, Why is she wearing that dress and why is she talking to Chuck? This Pucci minidress was perfect. It was olive green with zippers on it. It was very, very lux and this perfect transformation of Jenny from the block to Jenny owning the block.”
Episode: 304. Chuck brings Jenny to the aforementioned movie premiere to get Blair’s attention. Daman Says: “We see Chuck in formal attire quite a bit, but this — when he escorted Jenny, in the Pucci dress I already mentioned, to a movie premiere — was a special moment. He was trying really hard to make Blair jealous, so I conjured up images of a young Sean Connery as James Bond. Chuck never looked so chic or embodied old Hollywood glamour more than in this simple white dinner jacket, bow tie, and black tux pants.”
Episode: 312, which focused on the denouement of Serena and Tripp van der Bilt’s affair (car accident!), but also showed Jenny fully grown into leader of the high-school pack. Daman Says: “In this outfit, Jenny’s becoming the queen bee of the school. It’s this Oscar de la Renta motorcycle jacket, but it’s covered in clear sequins. She’s in a Gucci navy wrap dress. So she’s wearing Oscar de la Renta, Gucci, and a $30 knit hat. It just kind of feels like that ideal combination of unattainable couture mixed with very attainable Brooklyn taste.”
Episode: 317, trying to help Chuck save his hotel, Blair offers herself up to his uncle, Jack Bass. Daman Says: “This taupe chiffon Matthew Williamson gown with the beaded halter top was what Blair wore when she was sacrificing herself to Jack Bass. It was a difficult dress to find. We wanted a feeling of a warrior woman going to stand up for her man, but also the feeling that she’s a frail person susceptible to the evils around her. We wanted a combination of sacrificial lamb and Joan of Arc. The neckline of this dress almost looked like a breastplate, and that was giving off a Joan of Arc [vibe] for me, so it was one of those moments, Like, ‘How can I find a vulnerable dress and Joan of Arc at the same time?’ But I did.”
11 Best Gossip Girl Looks from the Show’s Designer