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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