Singer studied marketing at the Fashion Institute of Technology, where she was the first female graduate of the four-year honor program.[1] After graduating college, Singer took part in a traineeship program at Macy's and later became a buyer for the department store chain.[2][3] She also worked in sales management for the fashion companies Calvin Klein and French Connection.[3] In 1986, Singer started her own wholesale clothing business RMS Fashions, Inc. Together with her former husband Mario Singer, she founded a jewelry company named True Faith Jewelry in 2005.[4][5]
Singer joined as a cast member on the first season of Bravo's television show The Real Housewives of New York City. She remained on the show for thirteen seasons.[6][7] Singer's thirteenth season, which aired in 2021, drew the lowest ratings in the show's history.[7] In 2022, Bravo announced it would reboot The Real Housewives of New York City with an entirely new cast, while simultaneously greenlighting a separate series featuring some of the original cast members.[8] Behind-the-scenes tensions during and after the thirteenth season, including allegations of racially insensitive comments by cast members during filming, contributed to the network's decision to move forward without the original lineup.[9]
Singer starred in the first season of The Real Housewives Ultimate Girls Trip, a spin-off featuring various women from The Real Housewives franchise, that premiered on Peacock in November 2021.[10][11] She starred on the fourth season of The Real Housewives Ultimate Girls Trip, which was released in December 2023.[12]
Between 2009 and 2010, Singer sold two jewelry collections on the HSN.[13] In 2010, she also launched the skincare line Tru Renewal, which she relaunched as Ageless by Ramona in 2018.[14][15] In 2011, Singer launched her pinot grigio wine, respectively, Ramona Pinot Grigio.[16][17][18] In 2012, she announced a red wine partnership with Opicio Wines, Ramona Red: Sangiovese Merlot Blend.[19]
Singer's memoir Life on the Ramona Coaster was published in 2015 by Post Hill Press.
As of 2018, Singer rents out her Southampton mansion for $165,000 per month.[20]
In February 2026, Singer was announced to appear in the upcoming E! Network docuseries, The Golden Life. The series will follow Singer as well as former Real Housewives alumni Luann de Lesseps, Sonja Morgan, Kelly Bensimon, and Dorinda Medley uniting in Palm Beach, Florida.[21]