When Cruel Intentions premiered in 1999, it was an unexpected success at the box office. Putting Reese Witherspoon, Sarah Michelle Gellar and Ryan Phillippe on the world’s radar, the film was loved for its salacious plot, its stellar line up and perhaps above all, its costumes. Though, at the time the clothes worn by the ultra-privileged Upper East Side teens in the film were nothing out of the ordinary. Their ensembles were quintessentially 90s: sleek, simple, slightly boxy cuts and minimalistic to the core. But to watch the movie 25 years later is to appreciate the true stroke of genius these costumes really were. Timeless in every sense, the film’s costume designer Denise Wingate managed to capture the nuance of each character in pieces we’re still coveting in 2024.  

But say the fictional cast of Cruel Intentions were around in 2024, running around Manhattan and pulling their sneaky, underhanded tactics on one another, what would they be wearing? In an attempt to answer the question, we’ve raided the racks of The Galeries’ retailers, and these are our picks. 

Kathryn Merteuil 

Conniving and ruthless, Kathryn was often dressed in chic, soft pieces that bellied her dark side. This slip dress from Miaou is very 90s — elegant and simple but made sensual by its body-skimming cut and mesh panelling — and just a little contemporary thanks to its print. 

Miaou Gia Dress, $440 from Incu, Ground Level 

Sebastian Valmont 

Leaning into quiet luxury before it was a thing, Sebastian was often dressed in luxurious, impeccably tailored pieces in dark hues. This simple black knitted sweater from A.P.C oozes Upper East Side wealth, all the while being completely understated.  

Christian Jumper, $350 from A.P.C, Ground Level 

Annette Hargrove 

More innocent than her peers, Annette’s wardrobe was confidently soft and sweet. Pastel hues were prominent, as were more conservative cuts and silhouettes. Paired with a matching mini skirt, this pink cardigan is Annette Hargrove if ever we’ve seen it.  

Fiji Flower Pink Mini Ribbed Merino Cardigan, $375 from Ganni, Ground Level 

Cecile Caldwell 

As a newcomer to the world of New York City wealth, Cecile is spoiled and naive, and her wardrobe is the epitome of Upper East Side preppiness. This knitted vest puts a cool spin on Cecile’s slightly conservative primness.  

Dani Vest, $115 from Blanca, Ground Level