Former Calvin Klein Employees Reveal What It Was Really Like Working with Carolyn Bessette Kennedy in the ’90s

Former employees of Calvin Klein are sharing what it was like working at the fashion house in the 1990s, around the same era as Carolyn Bessette Kennedy.

Bessette Kennedy, who worked as a publicist for the brand until she left in 1996 to marry John F. Kennedy Jr., later died in a 1999 plane crash at age 33 alongside her husband, who was 38. Her time in the fashion world has recently been revisited in Ryan Murphy’s new FX series Love Story, prompting former staffers to reflect on the culture and strict office expectations they remember from that period.

In a TikTok posted Tuesday, Feb. 17, Kara Mendelsohn said she worked at Calvin Klein in the late 1990s, after Bessette Kennedy had already left. Mendelsohn described an environment with tightly enforced appearance rules that she believes would surprise people today.

According to Mendelsohn, employees weren’t allowed to wear nail polish, and makeup had to stay “extremely minimalist.” She said the overall look throughout the office mirrored Bessette Kennedy’s signature style: thin eyebrows, neutral tones, and hair often pulled back simply. Jewelry, she added, was expected to be understated, and anything that seemed too noticeable could be questioned.

Mendelsohn also pointed to a detail from Love Story that she found misleading. She said the show depicts Bessette Kennedy receiving red roses at work, but in her experience, non-white flowers weren’t permitted at employees’ desks. Mendelsohn recalled that reception areas featured white calla lilies and said the office maintained a consistent white-flower rule to match the brand’s carefully controlled image. The series itself acknowledges that red roses would violate the office’s standards.

Beyond appearance guidelines, Mendelsohn claimed staff were discouraged from interacting directly with Calvin Klein. She said employees were expected to stay focused on their work and avoid approaching him for casual conversation.

Another former employee, Mary Beth Kelly, also shared her memories online, saying she worked on the same floor as Bessette Kennedy, though in a different department. Kelly described her as warm and approachable, pushing back on the idea that she was distant. She remembered Bessette Kennedy as kind, down to earth, and consistently striking in person. Kelly added that, in her view, Love Story captured the feel of the office environment accurately.