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Why Bill Cunningham was a rare creature in fashion

Bill Cunningham in his signature blue worker’s jacket. Photo/Getty Images

Affable fashionista Bill Cunningham takes readers behind the scenes in the world of haute couture.

Fashion mavens adored the 2010 film on New York Times photographer Bill Cunningham, showcasing his indefatigable, sunny persona as he cycled around the city snapping street style.

In an industry dominated by stuck-up practitioners, his optimism and infectious smile couldn’t help but charm. He was also a rare creature who focused on people for what they wore, not who they were.

The documentary Bill Cunningham New York didn’t cover his earlier life, but after his death two years ago, at the age of 87, a manuscript was discovered in his modest apartment.


Fashion Climbing: A New York Life covers the years he worked in fashion before he started his photography career in the late 70s. As you would hope, it’s sharp, perceptive and sparkling with wit.

It opens with four-year-old Bill getting the daylights walloped out of him by his mother after she discovered him wearing his older sister’s dress.

His childhood, in suburban Boston, was drab, with his parents determined to block their son from any form of artistic expression, an attitude he condemns strongly.

Regardless, he searched for glamour anywhere he could find it, initially at church, where the women dressed in their best outfits, which were, in hindsight, pretty dreary.

Analysing women’s clothes became a lifetime preoccupation for Cunningham. So it was a red-flag day when the fashion department store Bonwit Teller opened a Boston branch and hired the teenager as a stock boy. “I thought I’d die of happiness!” he writes.

It was still Boston, though. When Bonwit sent him to New York for a brief training programme, he took to the city “like a star shooting through the heavens”. He quickly returned, for good, but was later fired for making hats and selling them on the side. He became an independent, opening a hat-making business in 1948 called “William J” to spare his parents’ blushes.

Cunningham’s roller-coaster decade of hat making was interrupted when he was drafted into the army in 1950, at the outbreak of the Korean War. Improbably, he assumed he’d be posted to France – and he was, where he ran millinery classes for officers’ wives and revelled in the arts.

On his return to New York in 1954, his profile rose, attracting clients such as actress Leslie Caron (“best not to meet famous people”) and Jackie Kennedy.

Cunningham sprinkles lots of delicious gossip throughout the book, but he also notes some ugly elements, such as the anti-Semitic talk that filled his New York salon. “All this damned side-of-the-mouth talk has made me ashamed of what high fashion is used for.”

In 1960, he closed the business and began reporting for Women’s Wear Daily, with the strict proviso he could be totally honest. His behind-the-scenes reporting of the frantic European fashion circuit, involving figures such as Coco Chanel and Cristóbal Balenciaga, are comedy gold.

Fashion Climbing leaves you in no doubt that Cunningham’s life was, as he frequently put it, “a hoot”. Against the odds, his creative freedom triumphed over the constraints of conservatism.

FASHION CLIMBING: A New York Life, by Bill Cunningham (Chatto & Windus, $40)

This article was first published in the March 2, 2019 issue of the New Zealand Listener.