#37. "Money is Cheap, Freedom is Expensive" Wise Words from Bill Cunningham
- Jessica C
- Sep 27, 2024
- 4 min read
Updated: Nov 24, 2025
“The surprise was a new generation’s discovery of the late Pauline Trigère’s beautifully constructed designs.” Bill Cunningham for The New York Times, November 14, 2004

"Money is cheap, freedom is expensive" . I adore these wise words from the very first street photographer, Bill Cunningham, undoubtedly the most significant fashion photojournalist of our era.
Cunningham once said, "If you don’t take money, they can’t tell you what to do, that’s the key to the whole thing." A documentary titled "The Times of Bill Cunningham" was created after director Mark Bozek conducted a spontaneous interview with Bill Cunningham in 1994. It is impossible not to be charmed by Cunningham's constant smile as he talks about his work and life philosophy. His infectious joie de vivre and genuine spirit come through as he expresses his passion for his work.
In the opening scene from the 2011 documentary “Bill Cunningham New York”, Anna Wintour remarked: “I’ve said many times, we all get dressed for Bill.” The documentary by filmmaker Richard Press and writer Philip Gefter of The New York Times gives a glimpse of Cunningham’s 50 year career of photographing people from the streets and events of New York.
Bill's journey at The New York Times began in 1978 with a collection of street fashion images that evolved into a recurring feature known as "On the Street," establishing him as a contributing photojournalist. His passion for unique styles prompted him to roam Manhattan in search of street fashion in New York. He later broadened his scope to encompass "Evening Hours," capturing images at exclusive high-society events.
Even though Cunningham regularly contributed to The New York Times, he never sold his photos to the newspaper. He believed that "If they pay you, they own you." This arrangement suited him well, as he led a modest life that allowed him to pursue his own interests. His small apartment at Carnegie Hall was essentially a compact studio lacking a kitchen and a private bathroom. The space was filled with file cabinets and boxes of his photographs, with a makeshift bed made of a cot on top of some boxes being the only furniture. He was always seen in a blue button-down workman's shirt, his distinctive attire. With his simple and unassuming demeanor, he preferred to abide by his own principles doing exactly what he wanted. It wasn't until later, when he was involved in a biking accident and required health insurance, that he became an official employee.
Bill Cunningham worked together with his neighbor and artist, Editta Sherman, on a photography project called "Facades." This project spanned more than eight years, beginning in 1968. Bill captured Editta in different historical outfits against iconic New York buildings, matching the period of their construction. The project expanded to include 500 costumes and nearly two thousand locations. For more images, visit a delightful blog curated by Lia in Brussels.
Bill was recognized as the Outstanding Photographer of the Year by the CFDA in 1983. He was also honored by the French government with the title of Officer de l’order des Arts et des Lettres. He was the sole media representative invited by Brooke Astor to her 100th birthday celebration. The street corner of Fifth Avenue and 57th Street was dedicated as the "Bill Cunningham Corner" following his passing in 2016.
Bill's photography philosophy centered around capturing people who dress with flair, emphasizing individuality over brand names. "It's not what you buy, it's what you do with it." He believes that true style lies in how you present yourself, not in the labels you wear. An article from "On the Street" on November 14, 2004, highlighted the newfound appreciation and discovery for the late Pauline Trigère's exquisite designs among a younger generation. I hope that Bill's insightful words will continue to resonate in the future.
In the course of my research, I came across an article that praised Pauline Trigère’s designs as the most outstanding collection compared to those of her peers. The article was featured in DETAILS magazine, where Cunningham served as a contributing writer and co-owner for a period.
DETAILS Story by Bill Cunningham
Some of the outstanding designers in America on this exalted plateau are Geoffrey Beene, Issey Miyake, Bob Mackie, Oscar de la Renta, Pauline Trigère and Bill Blass.
But it is Pauline Trigère’s collection that I would recommend to students so they could experience the superb technique of the dressmaking craft, the exquisite fabrics, and even more important, how these materials are worked into designs to flatter the figure of the client. Trigère’s collection is not about startling new designs, it is about the refining of ideas and establishing a perfection of fit for mature women within the limitation of ready-to-wear production. Let’s face it, young women can wrap themselves in a rug and look great. It takes a lifetime of dressmaking development to achieve perfect fit and stylishly enhance the wearer. It is this kind of ready-to-wear discipline that is scarce on both sides of the Atlantic.










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