When you land a gig as Anna Wintour’s personal assistant fresh out of college, it’s safe to say your career is already off to a charmed start.
After all, sartorial-inspired young women all over the country clutching their glossy Vogue magazines would kill for an opportunity like this one. But for Melissa Skoog, it was merely a classic case of luck and timing—one that ultimately helped shape Skoog’s adventurous journey in the world of fashion and entrepreneurship.
After eight months and several dead-end interviews with the HR department at Condé Nast post-graduation from the University of Illinois at Urbana-Champaign, Skoog finally received a call-back saying she could have a six-month internal temp position as a “rover,” if she could move to New York in three weeks. Despite no guarantees for future employment, Skoog packed her bags, moved out of her parents' Hinsdale home, and moved in with her older sister in the Big Apple.
Her first day on the job, Skoog was told to report to HR. Anna Wintour was looking for an assistant, and they thought she would be great—the decision was obvious. Skoog’s duties entailed everything from putting Wintour’s newspapers in order to taking the infamous work-in-progress “book” over to Anna’s house each night. “I was successful in the position because of hard work and becoming very resourceful,” said Skoog. “I was told my first day on the job that there was no such thing as ‘no’ in Anna’s eyes, and I took that very literally and seriously.”
“Creative strategy and my network are my strengths, so that—along with connecting brands/concepts together and watching them take form—is what I love the most about my job.”
About a month into her job, Skoog was promoted to first assistant, managing all things personal and professional for Wintour. “I learned not to expect something from someone if you weren’t already doing it yourself,” said Skoog. “Anna never expected anything from herself that she didn’t demand personally.”
After two and a half years, it was time for a change, so Skoog became an accessories editor at Vogue. “The notion of the ‘it’ bag was created while I was in that role—around 1998,” recalls Skoog. “It was very cool to be a part of history when status bags and the idea of changing your bag regularly/seasonally became a thing!” Skoog eventually left Vogue to take on a larger opportunity as the Market Director at Marie Claire, but eventually resigned after a career-changing event.
While on a market appointment to see Banana Republic’s new collection, the brand's PR team asked Skoog what she thought of a handbag, so she was honest. “I suggested they bring back a style from their previous collection, but punch it up with color and materials so they would have a relevant silhouette,” said Skoog. A few weeks later, she got a call saying they were going to make the bag in nine colors and sell it for $38 in 375 stores across the country. “I could not believe I was able to create that kind of impact,” said Skoog. Soon after, she was recruited by the company, moving to San Francisco in 2000 to join the merchant team for Banana Republic’s women’s division.
After four years, Skoog left to become the director of PR for Prada back in New York. “Prada is where I really learned about branding and how important staying true to your vision is,” said Skoog. “I had the incredible fortune of working with Mrs. Prada and her ridiculously talented Milan team, traveling a lot in the process.” While that may sound like a dream job, Skoog left Prada and briefly tried her hand working for an Internet venture, but wound up broke and jobless by February of 2009.
Instead of feeling defeated, Skoog took advantage of her entrepreneurial spirit and began consulting for high-end brands like Loeffler Randall, Anna Hu Fine Jewelry, and Emanuel Ungaro. While finding her new career path, Skoog also found love and eventually got married. Within seven months, she gave her newly betrothed the option to stay in New York or move to Chicago, when he was approached to become a partner at a Windy City-based wellness company called EngagementHealth.
“To be honest, I was terrified when he chose to move. There was no job for me in Chicago, so I had to create it myself,” said Skoog. “I spent the first year working from Chicago on New York and London-based brands, but was forced to staff up and become an agency in February 2012 when we landed a major gig with LOFT.”
With a three-week old son and an apartment as an office, Skoog recalls her start-up period as one that was crazy, but not impossible. Her firm has steadily grown into a team of eight, all of whom work out of temporary office space on Michigan Avenue. With clients like Tiffany & Co., CH Carolina Herrera, and Shinola Detroit in her portfolio, it’s safe to say her fashion experience paid off.
“Finding time in my day to manage back-of-house office work along with the creative is a constant challenge,” said Skoog. “But creative strategy and my network are my strengths, so that—along with connecting brands/concepts together and watching them take form—is what I love the most about my job.”
While Skoog admits she would have had more opportunities in her industry had she stayed in New York—since fashion enterprises are largely based there—she’s very proud of what she’s accomplished in Chicago. And this aspirational go-getter isn’t going anywhere anytime soon.