The Devil Wears Prada, But She Wears Cartolina


July 7, 2026

Thirty Years After Assisting Anna Wintour, Melissa Skoog Leads Cartolina on Nantucket

Written by Rebecca Settar

 Photography courtesy of Melissa Skoog

Chicly dressed in a designer charcoal wool full length coat and running in 90 millimeter heels, Melissa Skoog quickly exited CHANEL’s Manhattan storefront, her arms full of shopping bags, while three employees carried more behind her. A black tinted-window car idled on East 57th Street and as the door was being held open by the driver, a group of New York City tourists stopped to gawk at what they could only assume was a celebrity running from the paparazzi post-shopping spree, and like any curious tourists would do, they all began taking Skoog’s photo.


“This was my mom’s favorite story,” said Skoog, the creative director of the clothing line Cartolina, who in 1996 got her first big break in the fashion industry by working as an assistant to Anna Wintour, then editor-in-chief of American Vogue, a job since made infamous by Lauren Weissberger’s New York Times bestselling novel The Devil Wears Prada, based largely on her own experience just a few years later.


In the blockbuster hit movie based on the book, actress Anne Hathaway portrays Andrea Sachs, a recent college graduate who unwittingly lands a position as assistant to an extremely demanding fashion editor played by Meryl Streep. On the heels of the release of the sequel film The Devil Wears Prada 2, it could be said that Hathaway is essentially playing Skoog, who confirms the original movie adaptation was “very real.” “It was 1,000% that stressful,” Skoog said. “Just like Andy in the film, I was running in heels everywhere.”


Being Wintour’s assistant came with its own perks, one being the proximity Wintour enjoyed to the most elite fashion designers, A-list celebrities and musicians. “Elton John was playing,” Skoog recalls of one notable “housewarming party,” an elaborate monthly celebration Wintour would host to commemorate each magazine issue. It was hosted in, of all places, the bedroom of Gianni Versace’s Manhattan townhouse, in view of a custom-painted Basquiat mural.

“Anyone you can imagine—every major celebrity you can imagine—was there,” Skoog said.Working the card table, Skoog saw paparazzi camera flashes just before a strikingly handsome man walked in the door. “And then all I hear is, ‘Excuse me, do you have a card for John?’ John was John F. Kennedy Jr. “I was in this three-way conversation with Gianni Versace and JFK jr., and I’m 23 at the time,” Skoog laughed. “And I thought, this is outrageous. And it was like that every month.”


“I truly believe that she created the cultural zeitgeist and the meaning of luxury through the lens of Vogue," Skoog said. "She created this world of beauty and refinement and culture and knowingness that I think, especially in the 90’s, when you thought about the finest things in life, the most interesting, coolest trends, it all came through Vogue.”


Working for Wintour also meant proximity to fashion itself, and when Skoog “fell in love” with stiletto Manolo booties that appeared in the pages of British Vogue, she was able to get herself a sample pair, despite them not being available in the United States. Wearing them, “I literally felt like I couldn’t breathe,” Skoog said. But on one notably tired morning after endless 12-hour days on the job, she accidentally left them in the backseat of a taxi cab. I was beside myself. I must’ve looked forlorn because Anna asked me if I was OK and I told her what happened. A few weeks later, she put a box on my desk and said, “I’m sorry you had to be without them for so long. George [Malkemus] made you a pair.”


Wintour truly valued her employees. “She never asked anyone to do anything that she wouldn’t demand of herself. She worked as hard as she wanted you to work. She always showed me respect.”After finally leaving Wintour’s side, Skoog enjoyed a varied career in fashion, from Banana Republic to Prada, and eventually to forming an agency of her own, called Skoog Co. From there, she connected with Cartolina and its founder Margaret Anne Nolen, owner of Centre Point in downtown Nantucket.


As for her own connection to fashion, Skoog muses that what she loves about clothing is the power of it to create your mood. “It’s one of those most conscious but subconscious choices we make every single day as humans,” she said. “The way we dress really embodies how we feel.”Playfully coined as “elevated weekend,” the Cartolina line is a far cry from the all-black New York City uniform Skoog used to wear with Wintour. “This job has taught me to be more curious with color and print which I’ve never done before. It’s made me enjoy fashion again in a way that I haven’t in a long time."

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