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Fashion Climbing: A Memoir with Photographs

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The untold story of a New York City legend's education in creativity and style

For Bill Cunningham, New York City was the land of freedom, glamour, and, above all, style. Growing up in a lace-curtain Irish suburb of Boston, secretly trying on his sister's dresses and spending his evenings after school in the city's chicest boutiques, Bill dreamed of a life dedicated to fashion. But his desires were a source of shame for his family, and after dropping out of Harvard, he had to fight them tooth-and-nail to pursue his love.

When he arrived in New York, he reveled in people-watching. He spent his nights at opera openings and gate-crashing extravagant balls, where he would take note of the styles, new and old, watching how the gowns moved, how the jewels hung, how the hair laid on each head. This was his education, and the birth of the democratic and exuberant taste that he came to be famous for as a photographer for The New York Times. After two style mavens—the women who eventually gave Jackie Kennedy her famous pink Chanel suit—took Bill under their wing, his creativity thrived and he made a name for himself as a designer. Taking on the alias William J.—because designing under his family's name would have been a disgrace to his parents—Bill became one of the era's most outlandish and celebrated hat designers, catering to movie stars, heiresses, and artists alike. Bill's mission was to bring happiness to the world by making women an inspiration to themselves and everyone who saw them. These were halcyon days when fashion was all he ate and drank. When he was broke and hungry he'd stroll past the store windows on Fifth Avenue and feed himself on beautiful things.

Fashion Climbing is the story of a young man striving to be the person he was born to be: a true original. But although he was one of the city's most recognized and treasured figures, Bill was also one of its most guarded. Written with his infectious joy and one-of-a-kind voice, this memoir was polished, neatly typewritten, and safely stored away in his lifetime. He held off on sharing it—and himself—until his passing. Between these covers, is an education in style, an effervescent tale of a bohemian world as it once was, and a final gift to the readers of one of New York's great characters.

256 pages, Hardcover

First published September 4, 2018

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About the author

Bill Cunningham

4 books31 followers
Bill Cunningham, the iconic New York Times photographer, was the creative force behind the columns On the Street and Evening Hours. Cunningham dropped out of Harvard and moved to New York City at 19, eventually starting his own hat design business under the name "William J." His designs were featured in Vogue, The New Yorker, Harper's Bazaar, and Jet. While covering fashion for publications including Women's Wear Daily and The Chicago Tribune, he took up photography, which led to him becoming a regular contributor to the New York Time in the late 1970s. Cunningham was the subject of the documentary "Bill Cunningham, New York." His contributions to New York City were recognized in 2009 when he was designated a "living landmark."

Librarian’s note: There is more than one author in the Goodreads database with this name.

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Displaying 1 - 30 of 311 reviews
Profile Image for Jill Meyer.
1,188 reviews121 followers
July 21, 2018
I've often wondered why people write memoirs. (I also wonder why people read memoirs, but that's another review.) Memoirs are different than autobiographies because they usually only cover a time or relationship in a person's life. Memoirs can be boiling cauldrons of emotion if the writer decides to write about every feeling and action. Or they can be as buttoned-up as a winter coat, and give very little hint of personal feelings, while concentrating on what happened. The best memoirs, I guess, are a mixture of both.

The late Bill Cunningham wrote "Fashion Climbing: A Memoir with Photographs" before his death in 2016. Probably most people reading this review will know Cunningham from the fashion column he wrote for the New York Times. He would ride around New York City on his bicycle, taking pictures of - usually - young women who looked either "interesting" or fashionable. He was out pedaling and taking pictures until right before his death from a stroke at 87. He was a good photographer and a witty, perceptive writer. He also lived by his own rules, taking the jobs and associating people he thought most interesting. His book, however, is a look at his family and the early years of his career. It ends when he's in his 30's, and moving from his early career of hat designer and ending as a fashion writer.

Cunningham is a perceptive writer but he most certainly isn't a personal one. There's a look at his family in Boston - he's Irish-Catholic - who were a bit nonplussed at their boy's interest in wearing his mother's and sisters' dresses. He escaped to New York City, where he became a noted hat designer at a time when hat wearing was ending. He was drafted in the early 50's and was sent to France for his military service. (The alternative posting would have been Korea, at the height of the war.) He writes about his friends, associates, fellow designers, and customers.

But he doesn't talk about himself. He writes about events and people the experiences, but we really don't know how he feels about them. And, you know what, maybe that's okay. Sometimes I get sick of gushing feelings; is discretion bad? Bill Cunningham's memoir is a good one as long as you're not expecting emotional fireworks.
Profile Image for Autumn.
1,024 reviews28 followers
October 17, 2018
The astounding adventures of a truly happy and original person who lived solely for their passion. Inspiring! Full of hot tea from the Hamptons in the 50s! Very specific about where you ate if you could no longer afford the Automat! A gem.
Profile Image for Katie Shepherd.
67 reviews2 followers
October 4, 2018
I feel this was only published because of how well regarded Cunningham is now. His history is interesting and deserves attention however it is so much better served by the documentary. The book is chatty and gives some insight into the high fashion world but the prose leaves much to be desired. The best parts come in the first 50 pages. Cunningham's youthful excitement about fashion (much to his family's disgust) as well as his time in Europe with the military and his beginning as a designer of hats was worth reading. Most of all the book screams for more photographs.
I am looking forward to the new documentary narrated by Sarah Jessica Parker.
Profile Image for Joy.
892 reviews119 followers
June 17, 2020
I started this awhile ago and would have finished it sooner but I found it hard to concentrate. Not because the book was boring but because of all that’s been going on (the COVID-19 outbreak etc.). Anyway, I really enjoyed this memoir and recommend it highly! I’m not sure how I heard about it but Bill Cunningham was a very special, interesting man. Check this one out even if you have no interest in fashion!
Profile Image for Aria.
548 reviews42 followers
September 5, 2018
---- Disclosure: I received this book for free from Goodreads. ----

I just loved this book. I read it straight through last night, & it was ever so pleasant when I woke today, thinking of Bill & his life. I am only marginally interested in clothing as an art form & a skillful trade, not so much in what is pushed out in the glossy magazines or sold for mass consumption. Seems Bill was of a similar mind, but he had a burning passion that he followed w/ an honesty likely not since seen in the fashion world. Prior to this read I knew nothing of Bill except what little I recalled from having watched the film Bill Cunningham New York a few years ago. (I highly recommend it.) As such, this early part of his life was completely new to me.

Bill obviously had a ball telling his stories here. His voice is so distinct & clear it was as if he were sitting right there having a great time, just sharing tales with me. I had such fun reading it, even pausing when I thought I could hear him insert laughter. You can hear him smile when he tells these tales, & it's just beautiful. Such a unique soul. I'm so grateful to have been able to read this. He just makes me happy, which is exactly as it should be when one has been allowed to peek in on a well-lived life. As a matter of fact, I believe I'll go back & re-watch that film about him today. Thanks for being you, Bill.

Profile Image for Alisa.
484 reviews79 followers
February 13, 2019
A memoir just as spirited, whimsical, and exuberant as the author. For fans of Bill Cunningham, this is an unvarnished personal view of his early life. Bill grew up in a middle class Irish Catholic home in a suburb of Boston and as a child discovered his love of women's fashion by parading around in his sisters dresses, much to the horror of his family. He was shunned for it, but the irrepressible spirit in him refused to stay hidden. Young Bill embraced his unique and creative energy, and eventually found a way to leave home, ditch Harvard, and angle his way into the fashion industry in New York City. After a short-lived stint working at Bonwit, with pennies to his name he started his own business making hats under the label William J. What he lacked in business savvy he more than made up for in vision, creativity, and chutzpah. People watching was his fuel, and no better place than the galas and opera scene in NY. He befriended and attracted other like-minded souls seeking the thrill of the New York social scene. The stories he tells are fantastic, hilarious, and exemplifies his wildly creative mind and bohemian lifestyle.

His life takes a turn when he is drafted by the military post-WWII. Convincing his superiors that his linguistic skills (he taught himself basic French) and educational background (Harvard, but glossed over the fact he dropped out), he somehow pulls an assignment that lands him in Europe. Post-war the French were not keen on seeing American uniformed soldiers, so he again convinces his superiors that he should lead tours of American military men around France to acquaint them with life and customs so they could be accepted by the French people in post-war recovery efforts. Spending a significant amount of time in Paris, arguably the mecca of fashion design, he wiggles his way into runway shows and otherwise immerses himself further in his obsession with design and style. Bill would eventually return to Paris as a writer for Womens Wear Daily which was led by a mercurial editor who sometime clashed with Bill. They would part ways, and the rant about their differences in the book highlights what happens when two fiercely independent thinkers whose beliefs do not always match can go awry.

My disappointment in the book is that it ends abruptly. There is no segue into his later professional life for which he became widely known in recent decades, his life as a style and fashion photographer for the New York Times. Not even a hint of how he came to pick up a camera - it's a missing link that is probably just as colorful as his early career. But to be a follower of Bill Cunningham's On The Street series is to relish in surprise and the viewpoint of someone a little mysterious and unlike anyone else. This book doesn't unravel all the mystery, but helps me appreciate the man behind the lens a little more.
Profile Image for catherine ♡.
1,728 reviews170 followers
August 4, 2018
Actual Rating: 3.5

This book was actually quite interesting, and I wasn't sure that it would be for me, since I don't really have an interest in fashion...

But I still liked it - it definitely wasn't very emotional, but I learned a lot about culture and history along the way. There were some smaller anecdotes that seemed to be more personal and focused on personal growth, and I think I enjoyed these the best.

The photos were interesting to look at as well, as they really brought the story to life. In the end, I still don't think fashion is my thing at all, but this was a cool read.
Profile Image for Susan.
886 reviews5 followers
November 1, 2018
I'm kind of amazed that people haven't given this rave reviews because I found it to be a real page turner. And with each page (well, Kindle page), I wished I had met Bill Cunningham, fellow Bay Stater, because if he was as funny and droll in real life as he was on the page, you'd have an entertaining time. The book was like a friend was writing a letter with updates on his life and even though the stories went back 70+ years, it all felt very contemporary to me.
Profile Image for Kazen.
1,497 reviews315 followers
September 7, 2018
I'm not a fashionista by any stretch but I like me a good fashion documentary. The September Issue gave me a grounding in this topsy turvy world, after which I gravitated to Bill Cunningham New York . Cunningham was a private person, almost to the point of being a loner, so when I saw his posthumous memoir would be published the first week of September (natch) I snapped it up.

I knew Cunningham as a fashion photographer for the New York Times who did lovely On the Street videos. Treat yourself to a few here, here, and here - I dare you to watch without smiling. But before he picked up a camera he was a Boston boy who loved clothes, was drafted into the Army, and became a milliner upon his return. This memoir covers this early period of his life, so if you're looking for info on his photography or modern day notables like Anna Wintour you will be disappointed.

Cunningham starts with his childhood, growing up as part of an Irish Catholic family that did not approve of his playing dress up in his sister's clothes. In fact, his family approved of little that he did, from dropping out of Harvard and moving to New York to becoming a hat designer. Reading between the lines you can infer the pain that must have caused but Cunningham rarely discusses his inner life. We get all the action instead - working as a stock boy in Boston department stores, getting a lucky posting in France during the Korean War, and moving to New York and feasting his eyes on fashion.

The account appears to be written around 1970 and I had to keep reminding myself that. Modern me bristled at women designers being called "girls". He crashed party after party to look at the clothes the women were wearing, and I had to tell myself that 60 years ago that was more of a social faux pas than a criminal one.

Cunningham's writing is down to earth, and in the book he says kitchen-table style is preferable to sending the reader to the dictionary. As a result the tone is almost conversational and kept drawing me back to the page.

You will find many insights into his thinking here, such as why he never accepted anything while working, not even a glass of water. As the narrative catches up to the time of writing the telling slows down, going over each collection of hats, each year in the fashion world. While I would have liked more info about his early life I get the feeling that he only shared what he wanted to, and I respect that.

I enjoyed the read but if you've never heard of Cunningham this is probably not the place to start. First watch Bill Cunningham New York, become smitten, then read this memoir to fill in the gaps.
Profile Image for Annie.
109 reviews
October 27, 2018
What an endearing memoir! I have admired Bill Cunningham since I saw his documentary a few years ago and I couldn't wait to read this. I wouldn't describe fashion one of my particular interests, but Bill is such a genuinely lovely and interesting person that I got much more than I expected from reading about his work in the fashion industry. Without sounding too cheesy, this is an inspiring and touching read - raw and honest and Bill's character and spirit really shine through. I highly recommend it to everyone because it isn't simply about fashion but about maintaining a positive perspective and embracing life during the hardships that come with following your dreams.
Profile Image for Marie.
481 reviews2 followers
October 21, 2018
This is the first time I’ve read a book containing photos without any captions- no explanation of who the subjects are, or the context of time and place. The author obviously loves fashion, but often comes off as a snob.
12 reviews
September 24, 2018
I loved Bill Cunningham so I was interested to read his memoir. But it doesn’t cover his whole life and it lost my attention at various times Can’t reakly recommend it.
Profile Image for Anton Koval.
70 reviews11 followers
February 10, 2020
The book itself is really good, but it should match your expectations. And that is to say it is not about photography (not a single page mentions it), however it is entirely dedicated to fashion and artist's admiration of it in times when he was women's hat designer (and craftsman). Overall a quick sight into Bill's background, how his aesthetic feeling formed and also how witty and kind the man was. The most memorable chapters for me were the ones that described his years as a starving artist in New York and the last ones where as journalist he had a chance to cover fashion weeks in Europe.
Profile Image for Jo.
740 reviews14 followers
September 22, 2019
4 stars for the first half, 3 stars for the second half.

I know nothing about New York society or social climbing, or fashion climbing, as Cunningham describes, and most of the celebrity/society names went right over my head. But what fun anyway!

I’ve loved Bill Cunningham since I saw a documentary about him made near the end of his life. He’s an intriguing character, and even more so now that I read about his youth and millinery career. Some of his stories made me laugh out loud. Hanging the furniture out the windows to make space for his hat show?!

After the book started talking about reporting on fashion shows I found it less interesting. But I liked Cunningham’s philosophy on dressing for pleasure and joy rather than dressing to impress other people (many of whom have no taste anyway).

I appreciated the photos even though I would’ve liked some explanation of some of them. But the hats he designed (like the octopus beach hat) really have to be seen to be believed. What a fascinating guy. I am still laughing at the idea of him trying to sell the conservative dowagers on his fanciful fashions.

I would recommend this to any fans of Cunningham or fashion.
Profile Image for Ryan.
52 reviews10 followers
November 14, 2018
A very fun read - Bill reflects on his time climbing the social ladder as a milliner
Profile Image for staykind.
206 reviews6 followers
October 9, 2024
great story , fashion history, funny & eductional
Profile Image for Laurie.
973 reviews48 followers
November 6, 2018
Born during the Depression to an Irish-American family with conservative values, Bill Cunningham’s penchant for fancy clothes and beautiful décor was discouraged- discouraged to the point of receiving a brutal beating when his mother caught four year old Bill wearing his sister’s organdy party dress. His interest- passion- couldn’t be kept down, however, and he devoted his entire life to fashion in one way or another. He worked in boutiques as a teen, became a sought-after hat designer in the 50s (who was put out of business by the fact that, come the 60s, no one was wearing hats anymore), crashed every high-profile party, became an on-the-scene fashion photographer- working for the New York Times at one point, and basically celebrated the beautiful. More than fashion, he was interested in style- the clothes and the hats and the jewels had to be worn with originality and elan.

The manuscript for ‘Fashion Climbing’ was found, neatly typewritten and put away, after his death. The memoir covers the years before he became a photographer. Even though he had his share of starving times he was always cheerful and greeted the world as a place of delight. He wasn’t all sweetness and light, though; parts of the last chapter ‘On Taste’ where he makes it clear that most women don’t have style, and that to carry of wearing high fashion one needs not just great posture and manners but ‘generations of good breeding’; after all, one ‘can’t slipcover a pig and expect it not to grunt’. Oddly, this opinion is in the same paragraph where he tells us that one of the day’s most elegant women was a prostitute not long before!

It’s a short book and a fast read, interesting to someone who loves fashion history. A number of black and white pictures (more would have been great!), of Cunningham and various fashionable women- these are not fashion show shots. Four stars.


Profile Image for Liz.
427 reviews1 follower
March 20, 2019
I loved this book, not just for Cunningham’s eye for detail and his ability to recreate the fashion world of the 1950s and 1960s, but also for his indomitable spirit; when called up for the Korean War-era draft, Cunningham was thrilled at the possibility he might be sent to Europe and, sure enough, he was. Taking time away from his barely launched millinery career, the designer ended up stationed in Paris, his real introduction to a fashion world still reeling from the Second World War. He astutely identifies this period as the time of the passing of “the Old Guard,” when fashion was solely the field for wealthy women (whom he calls “fashion climbers,” those who use clothing solely as markers of status, rather than sources of personal pleasure). Although he laments the disappearance of hats for women and the rise of ready-to-wear, he’s also describing the democratization of fashion. He observes the designers’ struggles to be creative *and* competitive, their battles with “the press,” and his own attempts to be a part of a passing world. His reminiscences of Paris fashion shows—Dior, Balenciaga, Givenchy—and the upstart Americans challenging them were fascinating. Finally, his passion for the art of clothing was moving: after years of looking for an audience for his own unique vision, he writes after seeing a pivotal Balenciaga show in 1958, “no one will ever again be able to influence my fashion thinking, for I have seen the proof of creative design, and it’s worth every drop of hardship to climb to the top” (220).
Profile Image for lisa.
1,739 reviews
September 20, 2018
"No human being should be afraid of another, although we respect his high position."

Bill Cunningham, or William J, as he was known in his designing days, says this to his first boss while he is being fired, and it seems a pretty apt summary of his philosophy of life. Initially I was very disappointed over the lack of photographs in this book. Despite what the subtitle may lead you to believe, there are only a few photos in the book, and most of them are candid shots of the author, and some of his friends in his early days in the fashion industry. I wanted slick pages, large, well-produced copies, and a ton of images to look at. However, the memoir is sweet, and funny. It's a great little snapshot into life in the fashion industry in the 1950s and 1960s. Bill Cunningham turned his obsession with fashion into a hat making business, and then rolled with the punches when ladies slowly stopped wearing hats in the early 60s by becoming a fashion writer to Women's Wear Daily. He later went on to write for other publications, and became known for taking candid street shots of New Yorkers. This memoir makes no mention of anything in Mr. Cunningham's life past the early 1960s (presumably because he died before he could finish it) so there is a sense of getting only a brief moment of his life at one period in time.

Once I got over the fact there this isn't much of a "memoir with photographs" it was a delightful read.
Profile Image for D.
121 reviews2 followers
September 8, 2018
Written during his lifetime, but published posthumously, Cunningham describes his early days in fashion. The intensely private man is always looking outward in snapping photos and spotting trends. While looking inward is something Cunningham may have done, without sharing what he sees there, we can't really know him.
Profile Image for Mark Fallon.
919 reviews30 followers
November 5, 2019
For decades, Bill Cunningham was known for his fashion photos for the New York Times. Not just the fashion shows and galas, but shots of people on the street who were introducing new fashion.

Of course, before that he had an amazing life - which he recounts in "Fashion Climbing". An enjoyable read about a wonderful human.
Profile Image for Patti Imhof.
14 reviews2 followers
September 8, 2018
A delightful read about Bill Cunningham’s beginnings in his world of fashion, style and taste. I admired his photography in NYT style section for years; he captured so much humor along with the fashion. I loved learning where he started!
Profile Image for Raquel.
833 reviews
April 2, 2023
A charming, self-effacing, and humorous memoir of the early years of Bill Cunningham's life, from his Boston boyhood working in the stock rooms of grand Boston department stores to his arrival in New York City where he scrapped through many lean years making hats and loving fashion. Disappointingly, this book ends in the mid-1960s, so we don't get to learn about how Bill became an institution at the Times, where his amazing multimedia columns were an absolute delight even if you aren't a fashionista. [Raises hand] I suppose the documentaries on his life fill in those details; this is more a book about the times and doings that made Bill Bill.

There's a reserve here; it's clear Bill dealt with a great deal of rejection and misunderstanding on the part of his family, but this doesn't dive deep into that. Instead, it's about Bill's outlook on life, which is one of taking in beauty and innovation in its many forms. He was able to see opportunity in even the most dire of circumstances (his chapter on turning military service into an opportunity to explore European fashion, for example, is a lesson to all in silver linings), and if I can approach life with a tenth of the sense of wonder and opportunity Bill had, I'll be fortunate.

We were blessed to have such a luminous soul. This book is a delightful document of optimism.
Profile Image for Rachel Pollock.
Author 11 books80 followers
August 16, 2019
I've spent a couple days thinking about how to write the review of this book.

I didn't finish it--his prose style is so pedestrian and precious that, once he was done working as a milliner, i didn't care what else came of his early career. But, that was maybe the last two chapters? So i read enough of it to feel like i can give it a rating.

If you are interested in a memoir of a flamboyant, spendthrift young man who tossed away a scholarship to Harvard after a year to traipse around making truly hideous hats, here you go. He writes like a middle school student and is deeply enamored with his own frivolity and utter lack of good sense. The details about mid-century millinery in NYC are interesting, but otherwise, it's a wash.
Profile Image for Alison Roberts.
112 reviews5 followers
April 10, 2020
I was so disappointed by this. I know Cunningham is a man of his time (aka tight lipped and doesn’t talk about unpleasantries or personal stuff) but I wanted to know more about Him then the industry at the time. Just like now it’s pretentious and out of touch, so nothing new. I enjoyed reading about his time in the military and it’s because it was the closest to “personal” he got. Upsetting because I love him so much but in the end I felt like I read 250 pages of information I didn’t care about.
Profile Image for Cassidy.
18 reviews
August 13, 2025
What an inspiring read! I learned of Bill Cunningham while I was in college but didn’t know much about him besides his work as a street photographer. Learning of his career as a milliner and fashion journalist in his early years was so delightful! He truly was a bright light, with such creativity, charm, & wit.
Profile Image for Gina.
874 reviews10 followers
August 3, 2019
Fashion Climbing is an interesting memoir, although there are many moments of over indulgence...call the editor!

I had no idea that Bill Cunningham had been a successful milliner. The bulk of the book focuses on his millinery business.

Cunningham is a bit of a snip -- railing against designers and department stores copying his styles and ranting about celebrities and society women who failed to pay him.
Profile Image for Joyce.
431 reviews15 followers
August 13, 2025
Earliest chapters were best, outlining his straight-laced Boston childhood, his madcap life in NY as a milliner, his time in the Army in Europe (surprisingly successful), and his lurking behind potted palms in the great couture houses to get a jump on the latest fashion. As the memoir continued I wearied of his judgmental tone about fashion and fashionistas. It was especially odd to hear him rail against the attention-seeking and ludicrous fashions that became the norm in his later life, given that he spent a lot of time in his youth making hats that looked like giant fish and clam shells.

It’s hard to imagine anyone more guarded about his personal life, about which we learn very little. He was ascetic and seems to never have had an apartment in NYC with an actual bathroom or kitchen.

Overall, I think the documentaries about his life as a photographer were more endearing than this book. In particular I found the grainy, black-and-white, caption-less photographs a disappointment.
Profile Image for Lucy.
831 reviews208 followers
April 15, 2021
I thought I'd love this but it jumped around a bit too much for me and had constant name dropping. I wish we'd read more about his photography later on in life.
Profile Image for Shelby Stevens.
85 reviews5 followers
February 21, 2023
love this man's story and passion and appreciate this text simply as a historical piece and many slices of the past
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