Every now and then a leader within retail rises up and becomes the person to watch. They grab headlines. They make bold decisions. They shift the focus of retail — even if it’s only for a short period of time.
But then what happens? Sometimes the biggest names get to a point where they don’t snag headlines (or do so for all the wrong reasons). Or they leave retail altogether. Some stay involved, but prefer to take a behind-the-scenes approach to how they influence the industry.
Once upon a time these were the movers and shakers in retail. These people not only decided the direction of their respective companies, but in many cases they determined the path of pop culture.
Here are five people who led retail, and where they are now:
1. Jenna Lyons
J. Crew hired Jenna Lyons straight out of Parsons School of Design and thus put into motion a series of events that changed specialty retail and influenced the way Americans dressed. At least for a while. Lyons was appointed the executive director of J. Crew in 2008, then president of the retailer two years later. By 2017, Lyons had exited after over 26 years with the company.
Her television show “Stylish with Jenna Lyons,” launched in 2020 on then-HBO Max and ran for only one season. Around the same time as the TV show, Lyons debuted her new false eyelash brand LoveSeen with makeup artist Troi Ollivierre. During a push to add thousands of beauty products to its assortment, Target added LoveSeen to its lineup in 2022.
But, those lashes weren’t moving, Lyons told The Cut, stating that the big-box retailer wanted her to have a national campaign for awareness. And that’s where The Real Housewives television franchise came in.
In 2022, Bravo announced Lyons as a “Real Housewives of New York City” season 14 cast member. The role, Lyons thought, would give her the opportunity to increase her brand awareness.
But will Lyons remain a reality television star? In mid-November she appeared on “The Tonight Show Starring Jimmy Fallon” and played coy about a potential return to the show, not fully confirming or denying her ongoing participation in the series.
A week later, news broke that an executive at private equity firm Blackstone will spin out a team to create an independent brand strategy agency called FundamentalCo. Bloomberg reported that Lyons will be joining as the firm’s executive creative director.
2. Ye
Ye, previously known as Kanye West, made large waves in the retail world through his partnerships with Adidas and Gap.
The rapper had his hands in the fashion world for years, beginning with his time at Fendi as an intern alongside Off-White founder Virgil Abloh in 2009. In 2013, Adidas swooped in on Ye’s collaboration with Nike, and helped him launch the Yeezy Season 1 fashion line and the Yeezy Boost shoe franchise. The years that followed proved to be extremely successful for both Adidas and Ye.
Meanwhile, in 2020 Gap Inc. announced a collaboration between its namesake brand and Yeezy. What was expected to be a lucrative endeavor showed signs of trouble early on with sporadic drops, then accelerated when Ye went on social media, podcasts and television interviews with antisemetic comments and conspiracy theories. In September 2022, Gap announced that it was ending its Yeezy Gap partnership.
There were similar problems at Adidas. The retailer dropped Ye in October 2022 over hate speech and went on to sell Yeezy stock to clear inventory. The selling of leftover Yeezy merchandise went better than expected, and by this October the athletics retailer anticipated an operating loss of 100 million euros ($105.3 million at the time) for the year, down from its initial forecast of 700 million euros.
Also in October, The New York Times reported that Ye’s time at Adidas was marked with him making antisemetic and sexually offensive comments and displaying erratic behavior.
Ye continued to design with his own label, and held a secret fashion show for Yeezy Season 10 in Los Angeles in 2023.
Ye was recently named Billboard’s Top Gospel Artist of 2023 for the third year in a row.
3. Andy Dunn
When Andy Dunn co-founded Bonobos in 2007 it was the start of a new wave of DTC companies that were reaching out to consumers through their own websites, hip branding and a goal of disrupting retail.
A decade later and Bonobos was purchased by big-box retailer Walmart for $310 million. At the time, Walmart was snapping up a number of online retailers including Moosejaw and ModCloth and appointed Dunn to oversee those digitally native brands.
In 2018, Dunn stepped down as Bonobos’ CEO. A year later, Walmart announced that Dunn was leaving his remaining position as head of digital brands.
Dunn went on to write the book “Burn Rate: Launching a Startup and Losing My Mind,” regarding his bipolar I diagnosis and is currently a mental health advocate.
“My bipolar disorder was cloaked, not as symptoms of an illness or a condition, but symptoms of a job,” Dunn said during a TED Talk this spring regarding his time as an entrepreneur leading Bonobos.
Bonobos was sold by Walmart in April to brand management firm WHP Global and apparel retailer Express Inc. for $75 million. Two months later, Dunn returned to Bonobos in an advisory role.
Dunn also co-founded DTC company Monica + Andy with his sister, Monica Dunn Royer. The organic baby and essentials company this year partnered with Walmart.
4. Rachel Shechtman
In 2011, Rachel Shechtman founded Story, a boutique retail space in New York City’s Chelsea neighborhood that had a magazine-style monthly rotation of merchandise based on a theme.
Seven years later, Macy’s bought Story and Shechtman joined the retailer as its brand experience officer. The concept was set to give Story a “national stage” to “create impact at scale” she said at the time. By 2019, Macy’s had introduced Story and its rotating method of curation to its flagship at Herald Square and 35 other stores in 15 states.
Story’s shop-in-shop had partnerships with retailers like Dick’s Sporting Goods, and Shechtman led efforts with another of Macy’s concepts, Market by Macy’s. The Story concept sputtered out, though, and Shechtman left Macy’s in 2020.
After exiting the department store she returned to her consulting career, working with a number of brands and retailers including Lululemon, LVMH and Hodinkee.
Shechtman in October 2022 was named The Brooklyn Museum’s first Entrepreneur in Residence. The two-year program looks for ways to enhance the visitor experience. Shechtman works across departments to test new ways to engage with visitors and brings in external partners to work with the Museum’s retail and programming teams.
Shechtman also sits on the board of experiential toy company Camp.
5. Mickey Drexler
If you wore Gap in the ‘90s, you can thank Mickey Drexler.
Gap was founded in 1969 as a store in San Francisco selling third-party brands. Decades later as CEO, Drexler was credited as the person who transformed the company through a number of initiatives including private labeling and founding Old Navy.
He stepped down from Gap in 2002. In an interview this fall with The Real Deal, Drexler stated that he was fired from Gap with one day’s notice
Drexler landed at J. Crew in 2003, and worked with the aforementioned Lyons to accelerate the company. In 2013, he said in The New York Times that, “She is, in my opinion, one of the most talented, trained, intuitive and commercial designers that I have ever met.”
In 2017, Drexler stepped down from J. Crew amid falling sales, even as he was recognized by analysts as one of the top American merchants in history. In 2019, Drexler announced his retirement as chairman of the company.
Meanwhile, Drexler’s son, Alex Drexler, launched an apparel shop in 2012 under the name Alex Mill. In 2019, Mickey Drexler joined his son’s retail business where he currently acts as chairman.
Clarification: This story has been updated to add information regarding Andy Dunn’s involvement with Monica + Andy.
