I didn’t watch Gossip Girl because it was relatable. I didn’t try to see myself in a single one of the characters. I was no more a Serena than I was a Jenny, no more Upper East Side than Brooklyn. The reason I kept watching Gossip Girl is because the clothes — in all their uptown, old world, old money glory as reinterpreted for primetime CW television — were a little tacky, something indulgent to behold. Like the characters, the wardrobes were unattainable, completely impractical and wonderfully hyperbolic.

Who the hell wears white tights in dirty New York City, for example? And why, for another. What was the point of so many superfluous hair accessories? What was the meaning of all those damn fur vests? I’m a fairly practical dresser; I was even more so in college. The clothes on this show were my happy, fantastical escape. I admit I shit-talked about them as much as I enjoyed them (Serena’s handbags were so bad! But what great dresses she wore…) and ultimately accepted all of it costume.

Now that it’s a million years later, the clothes still resonate with me in that same love/hate way. While looking at runways and racks, I find myself referencing the characters’ wardrobes without meaning to: This coat is very Blair, these loafers are very *Chuck’s personal shopper, this multicolored paillette dress is both very Serena and also The Rainbow Fish. In fact, it’s those three in particular I find myself thinking about most when I need to get dressed for an occasion that feels particularly “New York.” It’s either them or the fancy kids from Whit Stillman’s Metropolitan (who allegedly inspired the Gossip Girl series in the first place).

Because it’s fall, and there’s nothing quite like this city in the peak of autumn, it seemed apropos to put together three outfits in their honor, a re-imagining of what their characters might wear today.

First there’s Blair, the Queen Bee.

How to: Clash plaid three ways. Wear a turtleneck under a blazer. You get to sit higher on the steps if you add a waistcoat. The beret is mandatory (and if you’re not a beret girl, there’s always the headband). Because this is a “modern” interpretation, swap tall boots for the white tights and tell your laundry bill to thank me later.

Next we have Serena van der Woodsen, who opted to go second so as not to piss off Blair.

How to: Pair a dramatic coat with a flimsy dress and slick boots up to your thighs for warmth. Grab gloves before you leave the house because you’re Lily van der Woodsen’s daughter, after all. But don’t brush your hair — small act of rebellion.

Finally, there’s *Chuck’s personal shopper.

*I had a problem with Chuck ever since episode one (they couldn’t have written in another non-creep-to-women character for Blair’s complicated, heart wrenching, will-they-won’t-they-wind-up-together-forever love affair?) so I’d rather give all the sartorial love to his fan-fictional personal shopper with excellent taste in suits, loafers and pinky rings.

How to: Wear a Pepto-pink suit, or any suit other than your standard solid, with velvet slippers that pop hard in colored juxtaposition. Don’t wear a shirt under unless you need to, and if you need to (club rules?) then do a striped bandeau.

Okay, now it’s time to vote: which character would you be most likely to dress like in the event you were invited to eat yogurt at the top of the Met steps?

Photographed by Edith Young; Modeled by Reece Perkins of The Society NYC; you can follow her on Instagram @reecefperkins

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  • Cristina

    I don’t know that I’ll ever stop trying to get that “slept in for days” Serena hair and her trying not trying makeup look. #teamS

    • Aydan

      but so much shiny pink gloss!! but the shades were always the perfect bitten pink!

      • Nikelle

        The perfect pink.

  • Catie Marie

    And the STONES! Serena literally wore rocks the size of my fist around her neck… I don’t even want to know what her chiropractors had to say about that.

    • Amelia Diamond

      so many damn jewelz

  • Lucy

    i still love white tights and want some for winter… should i just not??

    • Amelia Diamond

      i think you *SHOULD* and just post a photo because i’ll never not admire it

  • Sandra Guedes

    The Blair outfit is PERFECT

    • Oana

      Amen to that!

    • Amelia Diamond

      it was EXTREMELY “vicarious” styling

  • Courtney

    YES. Also really weird because I was just rewatching/binge watching this show yesterday?

    • Amelia Diamond

      from ep 1?

      • L

        Yesss — season 1 was the best one imo

    • Andrea

      So freaky, I was also re-watching haha!

      • V

        me too! since ep .1
        and indeed serena’s bag are really really bad!

        • L

          SAME! …it was such a random decision — wonder if Netflix is somehow unconsciously influencing us all through as-yet-undisclosed subliminal ad techniques.
          May I recommend re-reading the NYMag’s “Reality Index” columns in tandem?
          They would recap each ep with “points” based on how ludicrous each one was. They are hilarious and so sharply observed and defo heighten the re-watch experience

  • ThePetiteBrunette

    Love this! I’m so sick of minimalist fashion.

  • Akosua Adasi

    I wanted to be a Blair but I’m definitely a Serena (with a hint of Vanessa). Serena was all about the boho, impractical outfits that seemed easier to wear (not much easier) than Blair’s layered, perfectly structured and put together looks. I love all three looks in this post but The Serena is hands down my favourite because that yellow fur coat is everything!

    • Amelia Diamond


      • Aydan

        SHE JUST EMERGED ON SHAMELESS US AS A NEW CHARACTER ON THE PREMIER LAST NIGHT!!!!!!!!!! (In a role I think will suit her VERY well!)

        • Amelia Diamond


        • Eliza

          YES! And her character’s name is still Vanessa?!

  • Ulricha Ferdinandsen Bodenhoff

    THIS IS EVERYTHING ❤️❤️❤️ thank you

  • Maren Douglas

    Ughhhh Blair all the way. Recently rewatched from season 2 and on… just for the clothes. But maybe a little for chuck and Blair too?

  • Courtney Johnson

    wow, just bought a beret the other day due to some blair inspo- gg is always on my mind

    • Amelia Diamond


  • tmm16

    Yellow/purple is a color combo that should deff be used more IMO. Love that DVF coat.

    Also definitely binge watching Gossip Girl this weekend ’cause of this lovely, inspirational post.

  • Autumn

    Personally, I would wear the yellow jacket (which is everything!) over the pink suit.

    • Amelia Diamond

      i fell in love with that jacket hard

  • I’ve never seen a single episode of gossip girl but I very much appreciate those ultra-metallic boots. Very Barbarella-esque.

  • Zoe

    Love it when you do TV or movie inspired fashion shoots!

  • Zoe

    LOVE IT when you do TV or movie inspired fashion shoots!

    • Amelia Diamond


  • https://uploads.disquscdn.com/images/d711b8e19972bd8d04b346c0fd009e6bf4941e3e338040671ee6f573c3081b37.gif
    But seriously, I don’t think I can possibly choose. These are all phenomenal outfits, with or without the GG association. xoxo

    • Amelia Diamond

      my heart!

  • Rosie

    I like the very specific standing brief for the model which demanded that only one foot be on the ground for the first two photos. In the third pic you can tell she’s like ‘but both feet on the ground? what is this why, it should be lifted’.

  • gwendomouse

    While I think the Serena outfit is amazing, I have to state the following in good geek tradition: The books are so much better! I was obsessed with them as they were coming out. So I was quite excited when I heard about the TV series, only to be sorely disappointed. Apart from the fact that Blake lively is not remotely as supernaturally beautiful as her character is described (and the fact that she is so beautiful rules her entire life, for good or for worse) the storylines are much cleverer, and the characters more threedimensional and believable. And yes, in the TV version, they are badly dressed, I always wondered if this was intentional or just down to the costume designers getting it wrong. Especially as the books often contain detailed descriptions of outfits that are spot-on for the characters. I much prefer your versions here.

    • Amelia Diamond


      • silla

        YASSSSSSSSSSSSSSSSSSSSSSSSSSS. I always wanted to see Serena in the high necked Pucci dress and turquoise boots from the first book!!! That outfit has always stayed in my mind as the REAL Serena. Although I totally copied her gold dress and black tights look from ep 1 for like, ALL my “going out” looks at that time.

        • gwendomouse

          I even tried to find an outfit like that on Ebay. Unfortunately I had to admit that Vintage Pucci is out of my budget.

  • Sophie

    would have appreciated an eleanor waldorf power suit and pearls look

    • Amelia Diamond

      you are so right that is missing!!

  • Nikelle

    That Selena outfit is so Selena without even looking at the article. I just watched an episode of GG this weekend that Blair wore white tights in and I thought, YES! So I urge you to not pass me on the street. I. Love. Her. Style.

  • Miss Crystal

    Team Blair foreverrrr. My closet ended up obscenely preppy from this show and I still have more coats than anyone living in Los Angeles should sanely own.

  • bananarama

    most disappointing moment of my life was the first day of high school when I looked around and saw three+ people in pajama pants but none in Blair-Waldorf-and-minions-level coordinated outfits

  • Sarah

    I always loved the clothes on this show – I remember I bought both a pink and a bright red coat because i like the coats Blair and her friends work to school. https://uploads.disquscdn.com/images/47e40a7fc5ad0880f3ac1ed2bc6820c6fb7bd35b7a99c40786b1fb0cbb72600f.jpg https://uploads.disquscdn.com/images/b59cf55918799aea8df64d27c6049b33cc708a06e23fe17daba13bd6d49a3815.jpg

  • belle

    Ohh…need to add Dorota, Jenny, and Georgina. I rewatched the *entire* series recently and I’m about to do it again…

  • Katy

    Amelia, this is perfect.
    And don’t worry, I still say/think “this is so blair” or “so SVW” when I shop, too. GG is one for the ages.
    I bought my favorite shirt–a short sleeve lace No. 21 button down with an anchor embellishment–because my mom said to me in the dressing room, “What would Blair Waldorf do?”

  • All of this. Win win win win win.

  • Jasmijn

    This totally inspired me to go for a Blair outfit today!

  • Mareike Borkowski

    Just bought a beret yesterday (although I’ll probably never actually wear it) and immediately thought of Gossip Girl! Might watch an episode or two tonight. In love with the pink suit. Been looking for a bold colourful pant suit for ages but I’m having trouble finding the right blazer shape.

  • chris

    this is man repeller now….? sad

  • chris

    this is manrepeller now…? sad

  • Ally Frankel

    These outfits are ON. POINT. and now I’m so inspired to re-watch

  • Serena. But only if I also inherit the model’s hair and complection.

  • Ciccollina

    An aside: I absolutely HATED Vanessa. She was such a creep. I was always like GO AWAY VANESSA! Nobody likes you, not even Dan!

  • Isabela Alves

    I’m in love with the purple Zara boots! The whole Serena outfit is perfect, btw.

  • silla

    If Gossipgirl was reimagined for 2017, I feel that they would replace the yoghurt with kefir.

  • Kate Miskuly

    wow where are those beetle earrings from in the last outfit??? they’re amazing

  • CHUCK ! loooove it all

  • I’m currently in the process of re-watching from the start and I agree, all of Serena’s handbags are AWFUL. Maybe controversial but I think her cotillion dress was disgusting.
    I need those purple velvet boots ASAP!

  • Ivona Iwarra Josipovic

    I love all the outfits! Where is the bag from Chuck’s story from? <3

  • Lucy Rose Wood

    These outfits are so much better than anything they ever wore on the show!!!

  • Diana

    your fashion sense stunning and you remind me of björk when she started

  • ‘Love it! can you believe it, but at university, I dressed more like Chuck! Now I categorise myself as a sort of Serena, but without the sleeping around!

    But most importantly, isn’t it disturbing that I even admit to having ever watched Gossip Girl? And worst of all, liked it!

  • Gossip Girl was the best show I watched in my teens, every time I find myself to watch it now I can only think about the outfits: they were so impressive, and really unrealistic (? sometimes)! I strongly agree on this sentence: “Serena’s handbags were so bad! But what great dresses she wore…”!!!
    BTW, these three outfits are great and so “bright” (yellow and purple, excellent!), I definitely would wear Blair’s and Serena’s!