Gossip Girl
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Haven’t you heard? Iconic teen drama Gossip Girl, which focuses on the lives of the elite Upper East Side private students (read: there’s plenty of deliciously dressed rich teens boozing, backstabbing and sniping at each other) is getting a reboot by streaming service, HBO Max. It’ll kick off eight years after the original website went dark, with 10 hour-long episodes. While it is still uncertain if the former main characters — Serena van der Woodsen (played by Blake Lively), Blair Waldorf (Leighton Meester), Nate Archibald (Chace Crawford), Chuck Bass (Ed Westwick) and Dan Humphrey (Penn Badgely) — will make an appearance, one thing’s for sure: the new series has big fashion and styling shoes to fill.

While we wouldn’t go as far to say that the characters were as sartorially iconic as Sex and the City’s resident trendsetter Carrie Bradshaw (played by Sarah Jessica Parker), the show served us six seasons (2007 to 2012) of amazing looks and undeniably influenced the outfit choices of thousands of millennials. In commemoration of the news, we’ve gathered 10 of the most iconic Gossip Girl fashion moments for you to reminisce and get inspiration from. They are still pretty relevant to this day.

You know you love us, xoxo.

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Blair and Serena are total #friendshipgoals. Despite their ups and downs (and which friendship doesn’t have that?), they always find a way back to each other. So the next time you’re heading out with your bestie, why not go matchy-matchy with your sartorial choices? Here’s how to do it right without opting for kitschy couple wear. Both adopted yellow tones: Blair went with a more feminine approach with a printed dress and mustard tote while Serena gave a more androgynous spin with a yellow tank, black shorts and chunky jewellery, finished with a yellow ribbon in her golden hair.


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Here’s another way to show off your friendship with your bestie. Choose a cute, well-designed dress — in this case, a sexy backless dress — and get a different colour each. Cinch it in with the same belt — but in different hues. Not only will this guarantee that both of you look right on point, it will also make a cute photo op to profess your undying love with each other on Instagram. Optional: Opt for the same pair of shoes — such as elegant golden pumps — to really channel B & S’ effortless style. Finally, use accessories to inject your personal spin — Serena went with a polka dot hairband and red wallet clutch for a more playful touch. PS: They’re wearing matching lipsticks too.



Just because your job or school dictates that you have to wear a uniform everyday, doesn’t mean you can’t give your outfit your own stylish twist. Take this picture of the students from Constance Billard School for Girls and St. Jude’s School for Boys. The ladies added their own flair with the use of various headgear, such as berets and headbands, as well as bags, such as an oversized envelope clutch (Blair) and a designer shoulder bag (Serena). The cherry on top? Striking calf-length boots of various leathers and shades. Even the men are not lagging behind with various coat and shoes options — checkered, navy, camel, take your pick.

Related article: The Best Knee High Boots To Try Out Now


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Fashion trends usually trickle down from the runway to the street. In this instance however, we’re suggesting that it’s the other way round. Well, almost — from TV to the runway at least. Here, Blair and her minions (quick refresher course, from left to right: Nelly Yuki, Penelope Shafai, Isabel Coates and Hazel Williams) are decked out in eye-catching colourful tights that ranged from neon pink to leopard prints, and we think it’s rather reminiscent of the F/W’18 trend, where the message was “leggings with everything”. Flashy, unapologetically brash leggings were spotted on models at the shows of Jeremy Scott, Tom Ford and Victoria Beckham, and even style influencers Kendall Jenner and Ashley Graham were seen in them in real life. Moral of the story? Be bold, because you’d never know if you end up being the inspiration for the next big thing.


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I don’t know about you, but Golden Boy Nate Archibald and Golden Girl Serena van der Woodsen was one of my OTPs (that’s “one true pair” for those who aren’t familiar with Internet speak) because of how good they looked together. The two were dressed to impress at the White party in The Hamptons (no points for guessing the dress code) during the season premiere of the show’s second season. We especially loved Serena’s outfit here because she was decked in a low-cut v-neck dress with gathered details that oozed Greek goddess sex appeal. Serena finished the look with a pearl cuff bracelet and a cascading silver headpiece that adds to her Grecian-esque look. Classy, yet sensual, elegant, yet playful — we could all learn a thing or two from this ensemble.


It might have been a coincidence that Blair encountered Chuck in Paris at the start of season four. But she definitely showed her former beau (long story short, he cheated, she left, he didn’t get to propose to her, and his ring got stolen after he got beaten up and shot by thugs — we know, drama) what he was missing when she sported this spectacular ruffled red dress from Oscar de la Renta, which she donned for a date with a French prince to a ball. Serena was not holding back with her style either — she went with an edgier, more androgynous vibe with a pair of striking electric blue culottes that was contrasted with a shimmering gold blazer that sported peaked shoulders and bejewelled pumps — nothing short of spectacular.


While Chuck and Blair’s (or Chair to you diehard GG fans) relationship was still in its infancy in season one, this scene perhaps alluded to a greater love story between the two. After all, both of them were decked out in the best and brightest spring colours — orange and yellow — and they looked harmoniously on point. If we didn’t know, we’d have thought they were twinning intentionally.


Remember those brief episodes when Blair and Dan Humphrey (spoiler alert: he is Gossip Girl) dated? Yeah, you probably didn’t as you were trying to suppress that storyline as a horrible memory. Be that as it may, we forgive Blair’s relationship choices, because how gorgeous does she look in this scene? This deep red dress with a sweetheart neckline and embellished shoulders plays up her porcelain-like skin and draws attention to her collarbone. It’s no wonder then that Lonely Boy wanted her.


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A floral sun dress is a summer staple that everyone should and would have in their wardrobe, especially with Singapore’s tropical climate. While we’re not, erm, a big fan of the neck ruffles that come with Serena’s rendition, we like the flowy layered material and the cheerful print, not to mention the super sexy chest cut out that will amplify your assets. And if you want to give it that Upper East Side spin, pair it with a pair of black gloves like what Serena did for hers. Sure, it’s extra as heck, but it gives a touch of elegance and mystery that will certainly get heads turning.

Related article: Dress Like A Force Of Nature With Brilliant Colours And Vibrant Florals


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There’s this perennial debate on whether you’re #TeamSerena or #TeamBlair. We’re more of a Serena stan, because her fashion choices are more eye-catching, experimental and stylish as heck. Case in point: For her wedding to Dan Humphrey during the season and series finale, she ditched the typical white dress and went with this strapless gold and white Georges Chakra couture gown that has a dramatic train that can literally stop traffic. Too gorgeous. Don’t get us wrong, we’re also loving Blair’s to-die-for Elie Saab light blue lace wedding dress (spoiler alert again: she finally married Chuck!) in the same episode too, but Serena’s dress takes the crown when it comes to this episode’s wedding fashion face-off.