The Surreal Life Story of an Eccentric Street Style Pioneer

© Bill Cunningham

Fashion Climbing chronicles the late Bill Cunningham’s unlikely ascent to fashion fame (including the moment he accessorised with rhinestone-encrusted chickens)

Attired in his bleu de travail with his camera slung around his neck, American photographer Bill Cunningham was a familiar figure on the corner of Fifth Avenue and 57th Street. Notoriously close-mouthed about his personal life, it was a surprise to discover he left behind two typewritten manuscripts of a memoir following his passing in 2016. Rather than demystify his image in an industry viewed as a glitzy snake pit, Fashion Climbing reinforces the street style pioneer as a guileless fashion enthusiast. In the book, Cunningham recalls his start as a stock boy for Bonwit Teller, his army years spent as a cultural tour guide for the troops, the highs and lows of designing fashion-forward hat collections under the name William J, and the colourful characters that populated his New York in the 1940s, 50s and 60s.

As a boy, Cunningham’s mother beat him for parading through the family home decked out in his sister’s pink, organdy dress, determined to “knock this artistic nature out [of him]”, and his conservative Boston family enrolled him in trade school. Yet, he exercised his imagination by transforming plain table legs into works of art with fanciful “curlicues and twists” and revelling in the designer clothes at department store Bonwit Teller after school. Eventually dropping out of Harvard to work at Bonwit’s New York flagship, Cunningham embraced the razzle-dazzle of New York City.

Determined to succeed on his own, he took to rationing out three spoonfuls of Ovaltine a day, pawning and repurchasing his bicycle to ease up cash flow, and bedding down in his workroom at night to stay afloat. A different writer could have spun a melancholy tale out of these years, but Cunningham’s memoir is far from sombre. Peppered with delightful colloquialisms such as “a real dilly,” “a real lulu,” and “you’d drop your teeth,” and stories of his Monday ritual of starting the week right by buying fresh-cut flowers, the text bears the signature voice that endeared him to readers of his On the Street column, which was published in the New York Times (where Cunningham worked for almost 40 years). Yet, despite an ample dose of whimsy, there’s also a backbone to this cosy memoir, with astute allusions to novelist Edith Wharton in his description of style skirmishes between New York’s old families and new moneyed “invaders”. 

In his foreword, Hilton Als praises the memoir’s Breakfast at Tiffany’s ambience, and he’s not wrong. Desperate to fulfil a weekend order, Cunningham’s friend pawns her boss’ typewriter for the cash – narrowly escaping discovery by throwing telephone books inside the hollow typewriter cover when the boss unexpectedly returns; a French dress designer feuds with their staid German landlady over the heating because she could only design in her underwear; Editta Sherman dons a feathered Swan Lake costume to dance the ballet of the Dying Swan during a full moon.

These madcap antics are only topped by Cunningham’s own: attending a Beaux Arts costume ball with two live chickens on rhinestone-encrusted leashes; hoisting all of the furniture of his studio out the window on ropes and pulleys to make room for a press showing; designing larger-than-life hats shaped like fruit, deep sea creatures, and menagerie animals; cutting up a woman’s white panties to create a turban in Southampton; and gatecrashing a show at the Waldorf Astoria where he hid out on a catwalk 70 feet above the ballroom floor to rejoice in the glorious gowns below. 

Fittingly published on the eve of New York Fashion Week, Fashion Climbing celebrates one of the industry’s fiercest advocates of sartorial joie de vivre, who established himself on the fashion ladder “not with refined dignity but with an angry howl”.

Fashion Climbing by Bill Cunningham is out now, published by Penguin.

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