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All Of The ‘Gossip Girl’ Characters Ranked By How Badly We Want To Yoink Their Wardrobes

Where can we buy all of Blair's headbands?

If there’s one overall set of TV wardrobes we’d like to nab, it’s Gossip Girl. Look, while Friends had some sartorial zingers (HI Rachel Green’s tartan skirt), Marissa Cooper had some cute-ish ensembles, and Fran Fran was obvs the glamest fashion queen Flushing has ever seen; if you take those singular characters out, you’re left with a whole lotta drab-not-fab, honey. 

We mean, we wouldn’t be caught dead in Chandler Bing’s baseball cap and bowling shirt, or CC Babcock’s bland suits (almost as beige as her personality), but give us any Gossip Girl character - even the boys - and we’d happily copy their style. Like, VERY happily. 

So if we had free rein on set, aside from giving Nate a good ol’ sloppy smooch and slapping Blair just once in the face (eek - the scandal!), we’d raid the wardrobe section. Can you just imagine it? There’d be racks of sequined dresses, girlish prom frocks, cute-as-hell preppy ties, pearls as big as our heads, resort outfits ready for the Hamptons, headbands for days. Oh dear lawd, it would be glorious. 

And it’s not just the wardrobes of Serena van der Woodsen and Blair Waldorf that would have us swooning. 

We’d totes rock a suave suit and tie combo like Chuck Bass (remember that baby pink blazer and red tie? We die). Or Jenny Humphrey’s edgy tartan twinsets (with black fishnets, of course). Yep, the whole damn cast was like a fashion plate ready to be devoured. And god damn it was delicious. 

So with the Gossip Girl reboot in the making and all those GG feels comin’ on thick and strong - we’re reflecting on the most fashionable fictional characters to ever grace our television screens. And just like the cattiness of Constance Billard School for Girls, we’ve decided to rank them all - because that’s totes something they’d do (especially one Blair Waldorf).

So without further ado, this is whose wardrobes we’d yoink in order of how damn cute they are....

1. Blair

OK, so in number one place, it has to be, oh-em-geeeeee it HAS to be, the Constance Queen Bee herself, Blair Waldorf (played by Leighton Meester). We mean come on, does it get any cuter than her? The tweed twin-sets with perfectly knotted neck scarves. The polka dot prom dresses and flirty A-line frocks. That little white Marc Jacobs mini dress she wore to the all-white party in the Hamptons. THAT sequined floral applique Elie Saab gown she wore as her wedding dress to Chuck Bass in Central Park. Waldorf was the Upper East Side’s undisputed fashion queen, she not only ruled the halls of Constance Billard but made them her runway. She’d take a men’s silk pajama set and sex them up with garter belts and pearls for no reason except the fashion, daaarling. She’d clash kitschy Moschino prints ‘cause she damn could. She’d wear plush peacoats with gloves and felt bowler hats. And of course, the defining feature of Blair’s look: a headband. She single handedly gave rise to the headband’s popularity again, making everyone want to top off their look with a headband. Give us any part of her wardrobe ANY day of the week. PLEASE.

2. Serena

But not far behind her is Blair’s bestie - and the equally fashionable - Serena van der Woodsen (Blake Lively). While the two shared many a major fashion moment together (remember their matching backless dresses whey they made up after a fight and celebrated the only way they knew how: with an outdoor photoshoot. STOP. But don’t), Serena rocked her own classic preppy style. The neat blazers and brogues, the tartan flip skirts, the cinched trenches, the peep toe platform heels - and the ultimate Serena style move, a tie! My God, the girl knew he way around a tie. And a hat, geez she knew how to rock a hat, too. 

3. Chuck

Coming in third place is Chuck Bass (but don’t tell him, he’ll be pissed). The Upper East Side’s resident bad boy is also Mr. Style, wearing some of the best outfits on the show. Rich velvet blazers with beautiful corsages, baby blue suits with gingham shirts layered underneath, patterned cardis, fancy socks, sexy suspenders, dandy suits, and that famous slicked ‘do. DAMN he had good style. And he wasn’t afraid to take risks either, a master at layering and clashing colour and print. Chuck Bass, we stan for your style.

4. Vanessa

OK, this may be controversial people, but we’re calling it: Vanessa Abrams’ style was bloody cool. Played by sexpot Jessica Szohr, we love the budding filmmaker’s quirky looks: super refreshing from the high-end threads of her female peers. And while her bohemian style did evolve to mirror Blair’s fancy fashion sense, she did once quip that she would not be wearing snakeskin Manolos anytime soon. That’s our gal. 

5. Eva

Is a fashion list complete without a hit of Parisian chic? We think not. Enter Eva Coupeau, Chuck Bass’s chic AF French girlfriend (played by Clémence Poésy). She had all those understated French fashion feels: the quaint shirts, the tea dresses, the cardigans, the high-waisted full skirts, and that damn “French Girl hair” that no one except French girls can nail (seriously, how?). Ah, oui oui, that was some très chic style. (PS we’d really like that Cartier watch Chuck gifts her. K, thanks, bye). 

6. Jenny 

Next up, sweet little Jenny Humphrey who turned out to be not so sweet after all. Dan’s little sis had the biggest style transformation on the show: going from a cute-as-pie preppy freshman to edgy Goth princess, trading her perfectly-pressed school uniform for frayed fishnets, lots of leather, even thigh-high boots (and that super smudgy black kohl, ahhh, who could forget that). While we’ll always be here for her major gothification (and that frothy yellow tulle gown she wore to the masquerade party), she can keep the ill-fitting boots.

7. Nate 

So while Nate Archibold was a goddamn dreamboat (HIII Chace Crawford), his fashion sense was a bit, well, blah. Like, it was cute and all - but nothing groundbreaking. He was just like every other hunky jock at a well-to-do private boys school: checked shirts, tailored suits, skinny scarves in winter and polos aplenty. 

8. Dan 

Before he was a sexy serial killer in You, Penn Badgley was the loveable, dark coffee-drinking, uber sensitive Dan Humphrey. And while we allll loved him, fashion wasn’t really his thing. Boy was too busy writin’ poetry ‘n’ all. SWOON. But we will say his signature vests were bloody adorable and vests are actually kinda cool again. So there’s that: an accidental trendsetter from the start. 

This article was written by Kassie Angelo.

Main Image Credit: Licensed by Getty.

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