HomeOur ObsessionsThe scandalous looks of Manhattan’s elite: Ranking the best dressed characters of ‘Gossip Girl’

The scandalous looks of Manhattan’s elite: Ranking the best dressed characters of ‘Gossip Girl’

We remember Serena van der Woodsen’s fashions for exactly the wrong reasons – her look was consistently hideous. As you might imagine, she doesn’t fare too well in our exhaustive ranking of the 30 best and worst dressed characters of 'Gossip Girl', ranked from Upper East Woes to Upper East Wows.

The scandalous looks of Manhattan’s elite: Ranking the best dressed characters of ‘Gossip Girl’

Have you heard the one about Blake Lively’s Met Gala gown? Apparently it was so big she had to take a party bus to the ball to fit her train inside. Granted, it’s not the best joke we’ve ever heard about the actor and is actually a painful fact (if Vanity Fair are to be believed). The gown in question is an elaborate Versace gown that some poor bastard apparently spent 600 hours embroidering the bodice of. It’s also a significant step up from the sort of hellish maxi dresses and postmodern bodycons that her Gossip Girl character used to horrify us with back when the show was the reigning queen of The CW.

We remember Serena van der Woodsen’s fashions for exactly the wrong reasons – her look was consistently hideous. Lively might be looking luxurious but we can’t ever erase the memory of her in a ghastly print and oversized hat soiling the good graces of the Upper East Side. As you might imagine, she doesn’t fare too well in our exhaustive ranking of the 30 best and worst dressed characters of Gossip Girl, ranked from Upper East Woes to Upper East Wows.

30. Serena van der Woodsen (Blake Lively)

When she isn’t flouncing about in a fedora she’s always wearing far too many paisley prints or an unfathomable volume of maxi dresses. Boho-chic was never chic, honey. Especially not on the Upper East Side.

29. Dan Humphrey (Penn Badgley)

Babe, chest hair does not maketh an outfit just as throwing a blazer over a scabby old v-neck doesn’t make you look like a lovable rogue with the next great American novel waiting inside you.

28. Agnes Andrews (Willa Holland)

Agnes couldn’t style for shit but at least she knew enough to burn Jenny’s hideous dresses in a dumpster fire.

27. Nate Archibald (Chace Crawford)

A man of such basic sartorial inspiration has only three looks: retail manager at an outlet mall, polo enthusiast, and overly eager gigolo. None of them were particularly exciting.

26. Rufus Humphrey (Matthew Settle)

A walking gravestone for the 90s grunge scene, Rufus’s look was somber but practical. Probably so he was ready to “rock” at whatever given moment he became relevant again and could wear his flannel collection with pride. But also, his leather blazer and button down combos make us want to die.

25. Bart Bass (Robert John Burke)

Bart wore the sort of suits that you’d expect a villain in a child’s cartoon to wear. His look says that he’s bad news, probably has wings hiding in the back of his suit jacket, and is the sort of heartless bastard who would slaughter his own grandma just to empty her piggy bank.

24. Carter Baizen (Sebastian Stan)

Fellas – if you’re going to throw on a suit, at least pair a tie with it otherwise you wind up rocking Carter’s hideous look which makes him look like an apprentice car salesmen who had to borrow his first suit from the boss.

23. Lola Rhodes (Ella Rae Peck)

Lola’s looks start off as a solid A+ but the closer she comes to being pulled into Nate’s sartorially challenged orbit, the closer her looks come to being a solid F.

22. Eric van der Woodsen (Connor Paolo)

Eric started out as a preppy Justin Bieber type but his style progressed to the point where he looked like a preppy Jonas Brother by the end of the series. That’s some serious character development, folks!

21. Cyrus Rose (Wallace Shawn)

Look, Cyrus wasn’t the snappiest dresser but we absolutely appreciate that he at least makes some effort with his style by staying consistent. The man is comfortable in his slacks and cardigans and that’s all that matters because the man is an absolute saint!

20. Vanessa Abrams (Jessica Szohr)

While other characters were rocking couture, poor old Vanessa was thrown through the sales rack at H&M for her everyday looks. There’s basic and then there’s Vanessa.

19. Jack Bass (Desmond Harrington)

If only Jack’s dress sense was as sharp as his wit, he’d be rocking an ensemble that doesn’t make him look like a bank robber on parole at all times.

18. Catherine Beaton (Mädchen Amick)

Imagine that Serena’s wardrobe is a Pokemon and Catherine’s wardrobe is the full evolution of it. It isn’t as hideous as it should be but Catherine could definitely do better for herself.

17. Damien Dalgaard (Kevin Zegers)

We have three words to describe everyone’s favorite Upper East Side drug dealer: Patrick. Bateman. Jnr.

16. Louis Grimaldi (Hugo Becker)

If you get hot and horny for Eric’s wedding look in The Little Mermaid then Louis probably caused a huge splash in your very own “magic kingdom” because his entire look appeared to be based around it.

15. Kati Farkas and Isabel Coates (Nan Zhang and Nicole Fiscella)

Blair’s minions have always and will always be the leading style icons for synchronized high concept looks of obsessive best friends everywhere.

14. Eva Coupeau (Clémence Poésy)

She’s chic! She’s beautiful! She’s boring as hell. We’ve seen origami napkins with more wow factor than Eva.

13. Olivia Burke (Hilary Duff)

Olivia was supposed to be a hugely popular movie star yet for some reason she dressed like a men’s rights activist protesting a Jessica Jones panel at ComicCon.

12. Dorota (Zuzanna Szadkowski)

Sure, she rocks a maids outfit for much of the show but she wears it well. What counts is that when Blair needed Dorota to go snooping for her, Dorota always knows how to wear a scarf and an oversized pair of shades to do so with class and mystery. She’s a gem!

11. Ivy Dickens (Kaylee DeFer)

Her look is as cheap and trashy as she is but we kind of love it.

10. Georgina Sparks (Michelle Trachtenberg)

Imagine one of Disney’s wicked stepmother’s had a child with a drunken satanic cult leader of an Upper East Side sect and you get Georgina and her boisterously evil wardrobe. Right down to her shady leather gloves and ever shadier oversized sunglasses.

9. Henry Bass (Alex Bento)

Blair and Chuck’s son is the snazziest little boy in the history of anything. Nate must be looking at this precocious little hellraiser in waiting and wondering why he can’t obtain even a quarter of the chic of a six year old boy. Choices, Nate! Choices.

8. Nelly Yuki (Yin Chang)

Quirky, interesting, and effortlessly chic, Nelly is one of the best dressed tricksters to have ever taken on Blair.

7. Diana Payne (Elizabeth Hurley)

The body con dress lived and died with Diana Payne. Nobody in the history of anything anywhere will wear one with quite as much ferocity, swagger, or elegant classlessness.

6. Eleanor Waldorf (Margaret Colin)

There isn’t a single moment in Gossip Girl where Eleanor looks anything less than flawless. Mama Waldorf is a goddamn Upper East Side goddess, y’all!

5. Lily van der Woodsen (Kelly Rutherford)

Lily may as well dip herself in molten gold and have Karl Lagerfeld tattoo her asscheeks with his insignia because even when she’s on house arrest she’s still serving up high end luxury at all times.

4. Penelope Shafai (Amanda Setton)

Blair’s eternally loyal head minion was dedicated to her role right down to her everyday ensembles. Though Penelope remained in the shadows as a manipulator and saviour as and when Blair needed her, her sense of style often pushed her to the forefront.

3. Jenny Humphrey (Taylor Momsen)

We’d like to think that Jenny’s style evolution came as a result of Taylor Momsen simply waking up on the floor of some club before work each morning and refusing to change out of the clothes she turned up in. Either way, we love the punk princess look of her later, messier years.

2. Chuck Bass (Ed Westwick)

Bow ties have never been so sexy, friends! Never. It takes some serious cajones to pull off the ludicrous ensembles that Chuck does and make them look good but somehow he does and he does so effortlessly. He should totally look like a six year old boy at a christening but instead he looks like pure money.

1. Blair Waldorf (Leighton Meester)

Queen B is a queen for a reason, ladies and gentlemen. She’s absolutely flawless with outfits that don’t just reflect her impeccable taste but that also express a little about how she’s feeling and what shit is going down at any one moment. This is a woman who dresses for battle and her armor is good tailoring.

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Amy Roberts is a freelance writer who occasionally moonlights as a hapless punk musician. She’s written about pop culture for websites like Bustle, i-D, and The Mary Sue, and is the co-creator of Clarissa Explains F*ck All. She likes watching horror movies with her cat and eating too much sugar.

amy@filmdaily.co