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In 2007, Hyman and Fleiss met as sectionmates at Harvard Business School. They regularly met up to discuss entrepreneurial ideas, one of which was Rent the Runway. After seeing her sister overspend on an expensive new dress for a wedding, Hyman had the idea of offering dress rentals for women for special events. Long term, her plan was to offer women unlimited access to a designer closet they could rent from on-demand. Early on, Hyman and Fleiss pitched the idea to designer Diane von Fürstenberg as a rental service for her brand's website. She was initially uninterested, and suggested that instead they create their own multi-brand retail site. Hyman and Fleiss took her advice, and Fürstenberg signed on as one of the company's first designer partners. In 2009, the company received publicity from an article published in The New York Times. In 2016, the company began offering everyday clothing through a subscription model.
The company has received over $400 million in venture capital from investors including Fidelity, Franklin Templeton, TCV, Bain Capital Ventures, Highland Capital Partners, American Express, and T. Rowe Capital. In 2015, the company suffered negative press after the departure of several executives such as CTO Camille Fournier and Linda Honan (now of BBDO ). However, it was reported to have a positive bounce back by the end of 2016 with a Series E venture investment from Fidelity Investments and the launch of new physical retail shops. In 2017, Fleiss left the company to co-found Jetblack, a concierge shopping service. Fleiss remained on the board and Hyman remained as CEO. In March 2019, Rent the Runway received a new round of financing that increased its valuation to the unicorn level of $1 billion.
In September 2023, Rent The Runway profitability began to decline, as sales were reported as failing to meet soaring consumer demand after a disappointing quarter. In October 2023, CreditRiskMonitor reported that Rent the Runway was nearing a potential Chapter 11 bankruptcy filing.
In October 2025, Rent the Runway completed a recapitalization that reduced its outstanding debt to approximately $120 million, extended its maturity to 2029, and raised new capital through a combination of equity conversion and investor funding. The transaction included participation from Aranda Principal Strategies, STORY3 Capital Partners, and Nexus Capital Management, alongside a rights offering that generated an additional $12.5 million in proceeds.
In September 2026, Rent the Runway appointed Paige Thomas as chief executive officer, succeeding interim CEO Teri Bariquit, who became non-executive chair of the board. Thomas had joined the company as chief commercial officer earlier that year after previously serving as president and CEO of Saks Off 5th.