Lucinda “Cindy” Hollingsworth Holbrook, 85, of Oak Bluffs, Massachusetts, passed away peacefully on October 19th, 2022 surrounded by her children. She was born July 28, 1937 in Greenport, New York to the late Elizabeth (Morrell) and R. Lee Hollingsworth. 

Cindy led an interesting and adventurous life. Shortly after graduating from high school in 1955, she walked into the Eileen Ford modeling agency and was signed on the spot. Within a year, she was one of the most sought-after models, even gracing the covers of Vogue and Glamour in the same month. Her career as a top fashion model during the 1950s and 1960s (under her maiden name Lucinda Hollingsworth) offered her the opportunity to travel the world and work with the top fashion photographers of the time such as Horst, Avedon, Radkai, Rawlings, Dambier and Kublin, among others. During Cindy’s prolific career, she appeared on the covers of Vogue, Glamour, Mademoiselle, Charm, McCall’s, Sports Illustrated, and numerous other publications. In addition to her editorial work for these magazines, she was featured in major advertising campaigns for a variety of companies including Monet Jewelry, Revlon, Chanel, Balmain Parfums, Gilbey’s Vodka and Tricosa knitwear. Cindy was a memorable face of her generation, working alongside other top models including Suzy Parker, Jean Patchett, Delores Hawkins, Dovima, and Carmen Dell' Orefice.

After retiring from modeling, Cindy married and raised her three children in Greens Farms, Connecticut while still finding the time to pursue her varied interests and volunteer work. As bright, charming and funny as she was beautiful, Cindy was also very creative and accomplished when she set her mind to something. Having learned to sew at a young age, Cindy excelled at designing and making her own clothing, which always had a unique flair. She continued her education in fashion by attending design classes at Parsons. Another lifelong passion was gardening. She was a member of the Sasqua Garden Club and served a term as President from 1989-1991. Especially in her later years, she could be found most days working in her garden.

Cindy loved antiquing and once spent a three-week trip in England with a good friend visiting antique shops – a large freight container of her finds followed her home. She used her knowledge of antiques as Co-Chair of the Antiques Committee at the Fairfield Women’s Exchange, an organization that she enjoyed supporting for many years. Cindy also loved interior design and architecture. She designed, furnished and landscaped three wonderful houses in her last 30 years. Cindy’s favorite sport was skiing. She was an elegant and graceful skier who logged more than 2 million vertical feet of off-piste helicopter skiing with CMH in the Canadian Rockies over her lifetime. As elegant as she was grounded, Cindy was never afraid to get her hands dirty and was always building or fixing things in her woodshop. She probably owned more power tools than most men. Her family would routinely find things around the house that she “MacGyvered” with a bit of string or duct tape.

A long-time summer resident, Cindy moved to Martha’s Vineyard full-time in 2018. She worked as a volunteer at the Chicken Alley Thrift Store and joined a bridge group where she made some very good friends. Her marriage to George W. Holbrook, Jr. ended in 1994. She is survived by her three children, Megan Holbrook (Eric Vogel), Amy Holbrook and John Holbrook, and her brothers George (Teresa) Hollingsworth and John (JoAnn) Hollingsworth, as well as 14 nieces and nephews. She was preceded in death by her parents and her brother C. Thomas Hollingsworth. A memorial service will be held in Westport, Connecticut on December 3rd at 1 pm at the Greens Farms Church. A private family burial in Cutchogue, New York will follow. In lieu of flowers, please consider a donation to the Connecticut or Massachusetts Audubon Society.