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The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin'
In The Way You Wear Your Hat, author Bill Zehme presents a masterful assembly of the most personal details and gorgeous minutiae of Frank Sinatra's way of livingmatters of the heart and heartbreak, friendship and leadership, drinking and cavorting, brawling and wooing, tuxedos and snap-brimsall crafted from rare interviews with Sinatra himself as well as many other intimates, including Tony Bennett, Don Rickles, Angie Dickinson, Tony Curtis, and Robert Wagner, in addition to daughters Nancy and Tina Sinatra.
Capturing the timeless romance and classic style of the fifties and the loose sixties, The Way You Wear Your Hat is a stunning exploration of the Sinatra mystique.
Capturing the timeless romance and classic style of the fifties and the loose sixties, The Way You Wear Your Hat is a stunning exploration of the Sinatra mystique.
258 pages, Kindle Edition
First published November 1, 1997
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Displaying 1 - 30 of 77 reviews
April 25, 2010
A great, great friend of mine named Ed gave me this book as a gift more than thirteen years ago and I keep it nearby at all times, not so much to open up, but just to have as a reminder. The title page has quotes from Tennyson - "...How dull it is to pause, to make an end/To rust unburnish'd, not to shine in use!" - and from Sinatra - "Let's start the action!" - to which my friend has added, "In celebration of the wee small hours of the morning." I think that says it all.
July 24, 2015
This was a revisit. Enjoyable book with lots of good anecdotes about Sinatra and associates. Perhaps a little heavy on the hero worship but that's ok - even understandable in some circumstances. Sinatra, after all, was a larger than life persona with great artistry and exceptional talent.
June 1, 2010
Frank Sinatra as you would like to know him -- a biography revolving around stories, interviews, quotes, and photographs. As close as you can get to the man's thoughts on life without sitting down with him yourself.
The title made me think this was a guidebook, but it isn't. It's a biography, but not in terms of born here, died here, so much as this is what Frank did and thought, and here's a story or example to prove it. Well sourced. Zehme had Frank's input and blessing, as well as many of those close to him. If you're a Sinatra fan and haven't read this book, get to it.
After the first chapter, I didn't think I was going to like it or Frank. I stuck with it and I'm glad I did. After reading, you end up with a well-rounded glimpse at the man. Loyal doesn't seem to cut it. Let's say this: everyone deserves a friend like him.
The title made me think this was a guidebook, but it isn't. It's a biography, but not in terms of born here, died here, so much as this is what Frank did and thought, and here's a story or example to prove it. Well sourced. Zehme had Frank's input and blessing, as well as many of those close to him. If you're a Sinatra fan and haven't read this book, get to it.
After the first chapter, I didn't think I was going to like it or Frank. I stuck with it and I'm glad I did. After reading, you end up with a well-rounded glimpse at the man. Loyal doesn't seem to cut it. Let's say this: everyone deserves a friend like him.
August 10, 2020
I love learn about famous people's privent lives!
July 20, 2009
This book provides an interesting and personal glimpse into the life of one of America's greatest icons. Rather than being a typical biography that charts a person's life from birth to death, this provides chapters that are actually essays on various aspects of Sinatra's life. His singing career is of course covered in these essays, but the material really highlights Sinatra's way of life. Sinatra lived by his own strict code, and was actually somewhat insecure and afraid of being alone, so he surrounded himself with a constant party. The book is full of quotes from close personal friends and tons of great photos. A really entertaining read.
September 11, 2008
Great photos of an era & a life that people look back on fondly. If you look at the drinking (5th of Jack Daniels a day), the insomnia, & the women, his life looks sad. He did many good things & many bad things & some things that only mattered in that time & place & to his family. -- However as publicly as he fought (racism, photographers, reporters), he publicly & privately did a lot of good (some of which we will probably never know -- he kept it private). The writing comes off sometimes as a little star-struck but overall it was an interesting read.
February 24, 2008
The primary reason i like this book is because it has over 100 pictures, some of which have never before been released. However there's not much in the book about his film career, and little mention of his songs, and not much about his family. Most if not all of the pictures, have an interesting story, or at least the story behind the picture. So it's perfect if you want a very light-hearted look at the man and his life and so forth that only really scratches the surface of the man and his life, with many wonderful pictures
May 8, 2011
Great book. The format was a little strange at first, till I understood it was a question, answer, explanation setup. I did not know much about Sinatra before reading this, fascinating to see how he was really like and what he found to be important.
A great view of a time when adult entertainment was having a good time with friends, not a euphemism for XXX. You can do a lot of crazy things, if you do them with class and never really lose your cool.
A great view of a time when adult entertainment was having a good time with friends, not a euphemism for XXX. You can do a lot of crazy things, if you do them with class and never really lose your cool.
February 2, 2020
This book was uniquely done by the writer asking Sinatra before he died 30 questions about how to live life, augmented by vast interviews with all the people who knew Sinatra through the years. This book gives deep insight into the cocky lifestyle of Frank Sinatra. With 100 vintage pictures, and the vivid language and quotes, it gives the reader a colorful picture of the cool-cat era of the 1950’s, etc. I highly recommend this book.
March 30, 2016
If the goal of a biography is to give the reader the feeling of knowing the subject, this book succeeds masterfully. A collection of anecdotes, conversationally presented, creates a feeling of intimacy and familiarity with the Chairman of the Board. Not much history but story instead.
Wonderful. Exactly what I was looking for.
Wonderful. Exactly what I was looking for.
November 11, 2016
Uma coleção de textos sobre Sinatra, o livro faz você se apaixonar pelo cantor e pelo lifestyle da época.
É uma leitura gostosinha, uma biografia muito fácil de ler...
Pode ser um pouco repetitiva em alguns momentos por conta de ser uma coletânia de reportagens. Mas é bacana também para conhecer a época dourada de Hollywood :)
É uma leitura gostosinha, uma biografia muito fácil de ler...
Pode ser um pouco repetitiva em alguns momentos por conta de ser uma coletânia de reportagens. Mas é bacana também para conhecer a época dourada de Hollywood :)
April 14, 2019
I bought the book at a book-sale thinking it would be interesting to know more about Frank Sinatra. We do appreciate his music and I have heard some controversial things about him and Fidel Castro. It could be a good book but after reading about a third I just could not read another word about such a self absorbed person.
November 9, 2023
3.5 Stars
Took me long enough! 🥲 that speaks for itself on a con with the book, not always the most exciting read. But I learned a lot about Sinatra and his quirks. It’s more than a biography, it’s a sort of guide to living. Interesting advice and stories from ol blue eyes. Overall enjoyable.
Took me long enough! 🥲 that speaks for itself on a con with the book, not always the most exciting read. But I learned a lot about Sinatra and his quirks. It’s more than a biography, it’s a sort of guide to living. Interesting advice and stories from ol blue eyes. Overall enjoyable.
April 30, 2008
Matt made me read this before he would marry me. Frank was a stud. I might have a little crush on Frank Sinatra.
March 14, 2014
an entertaining read for any Sinatra's fan. I love Sinatra more and more after reading this book. his loyalty to his friends, his generosity to everyone, his love to his family.
June 25, 2014
If you need a guide on how to live your life, this is for you!
March 10, 2019
Sinatra was a looney.
April 22, 2021
Some of the best photos I’ve ever seen in a book. If you love Sinatra, you’ll love this book. I thoroughly enjoyed it.
September 12, 2022
At first, I had a hard time adapting - but I love the images and the organization of host story - got some of his music saved in my Spotify now
January 4, 2023
sinatra was an alcoholic and a womanizer. and this is proof most women in america have lost the art of livin'.
October 7, 2023
Fun read for Sinatra fans and those who feel like they missed out on an earlier era.
August 29, 2024
I think this book is good for Sinatra diehards but it would not be a good biography. It talks about Frank beyond his career but him as a person.
December 26, 2024
Not bad but I have read better life stories.
October 14, 2025
Good inside stories about how Sinatra approached everyday living.
May 5, 2020
I have a complaint about the mostly amiable “The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’.” It has nothing to do with Bill Zehme’s occasionally purple prose, or the sometimes overly fawning tone, or the rambling organization.
It’s the layout.
Many years ago, when I lived in the New York area and took the train to work, there were people who would put on a pair of special gloves before opening their New York Times or Wall Street Journal. Why? They didn’t want to stain their hands with newsprint ink.
I wish the publishers of “The Way You Wear Your Hat” had thought of this.
The many chapters – “Pallies,” “Style,” “Broads” among them – begin with a black page laden with white print. There are also occasional lists and anecdotes (“His New Year’s Resolution Toasts,” “Francis Albert Sinatra Recalls His Debut on Earth”) also done in white-type-on-black. And that’s not to mention the type itself, which veers between frilly headings, random copperplate boldface, and pull quotes (aside from the standard text).
It’s infuriating to read. It feels like a jumbled scrapbook presented by your overly enthusiastic uncle. You just want him to take a deep breath and get his stories straight.
Too bad, because “The Way You Wear Your Hat” has some good stories. There’s a complete backgrounder of how the Rat Pack formed (it was mainly Humphrey Bogart’s doing; Sinatra inherited it, but preferred to call it “The Clan”), how fastidious Sinatra was in fashion (the precision of his cuffs, his fondness for Yardley’s English lavender soap and the color orange), how loyal he was to his friends. It’s fine, as far as it goes. It would have made a fine article, and in fact, that’s how it started.
However, as a book it’s too much of not much. Even in 1997, when it was published – not long before Sinatra’s death – Sinatra’s ways had vanished in a mist of cigarette smoke and Jack Daniel’s (two of his favorite things). His voice was still a precision instrument, his albums part of the pantheon, but though he may have been able to teach younger generations a thing or two about manners, he comes across no less a throwback than the beatniks and longhairs he disliked. After all, when’s the last time you heard a woman described as a “broad”?
Sinatra is one-third of Zehme’s “Trinity of Cool,” along with Johnny Carson and Hugh Hefner, and though all three have something to teach in their diffidence and style, all three also seem part of a vanished age, like black-and-white visitors to our HDTV universe. (Carson, whose wit is timeless, probably comes off as the most contemporary.)
Zehme is a fine and clever writer – he once did a story about Warren Beatty in which he timed Beatty’s prodigious pauses – but he lays his admiration for Sinatra on thick. This isn’t a biography – it’s more slices of life – but it still feels distinctly one-sided. There are gentle reminders of Sinatra’s vicious temper, but they’re heavily cushioned with stories of the singer’s generosity and (occasionally) remorse.
If you’re looking for a Sinatra biography – as I am, something fair-minded and comprehensive (in other words, not Kitty Kelley’s “His Way”) – you’ll want to go elsewhere. If you want a book to browse through, “The Way You Wear Your Hat” will fill the time with some nice anecdotes. If you want to lose yourself in some classic performances, there are any number of Sinatra LPs to pull up on your favorite streaming service (or, if you want to go old-school, to place on your hi-fi).
And aside from all that, you may want to reset the type. Frank wouldn’t like it if your fingers are blackened. He probably would have worn those newspaper gloves.
It’s the layout.
Many years ago, when I lived in the New York area and took the train to work, there were people who would put on a pair of special gloves before opening their New York Times or Wall Street Journal. Why? They didn’t want to stain their hands with newsprint ink.
I wish the publishers of “The Way You Wear Your Hat” had thought of this.
The many chapters – “Pallies,” “Style,” “Broads” among them – begin with a black page laden with white print. There are also occasional lists and anecdotes (“His New Year’s Resolution Toasts,” “Francis Albert Sinatra Recalls His Debut on Earth”) also done in white-type-on-black. And that’s not to mention the type itself, which veers between frilly headings, random copperplate boldface, and pull quotes (aside from the standard text).
It’s infuriating to read. It feels like a jumbled scrapbook presented by your overly enthusiastic uncle. You just want him to take a deep breath and get his stories straight.
Too bad, because “The Way You Wear Your Hat” has some good stories. There’s a complete backgrounder of how the Rat Pack formed (it was mainly Humphrey Bogart’s doing; Sinatra inherited it, but preferred to call it “The Clan”), how fastidious Sinatra was in fashion (the precision of his cuffs, his fondness for Yardley’s English lavender soap and the color orange), how loyal he was to his friends. It’s fine, as far as it goes. It would have made a fine article, and in fact, that’s how it started.
However, as a book it’s too much of not much. Even in 1997, when it was published – not long before Sinatra’s death – Sinatra’s ways had vanished in a mist of cigarette smoke and Jack Daniel’s (two of his favorite things). His voice was still a precision instrument, his albums part of the pantheon, but though he may have been able to teach younger generations a thing or two about manners, he comes across no less a throwback than the beatniks and longhairs he disliked. After all, when’s the last time you heard a woman described as a “broad”?
Sinatra is one-third of Zehme’s “Trinity of Cool,” along with Johnny Carson and Hugh Hefner, and though all three have something to teach in their diffidence and style, all three also seem part of a vanished age, like black-and-white visitors to our HDTV universe. (Carson, whose wit is timeless, probably comes off as the most contemporary.)
Zehme is a fine and clever writer – he once did a story about Warren Beatty in which he timed Beatty’s prodigious pauses – but he lays his admiration for Sinatra on thick. This isn’t a biography – it’s more slices of life – but it still feels distinctly one-sided. There are gentle reminders of Sinatra’s vicious temper, but they’re heavily cushioned with stories of the singer’s generosity and (occasionally) remorse.
If you’re looking for a Sinatra biography – as I am, something fair-minded and comprehensive (in other words, not Kitty Kelley’s “His Way”) – you’ll want to go elsewhere. If you want a book to browse through, “The Way You Wear Your Hat” will fill the time with some nice anecdotes. If you want to lose yourself in some classic performances, there are any number of Sinatra LPs to pull up on your favorite streaming service (or, if you want to go old-school, to place on your hi-fi).
And aside from all that, you may want to reset the type. Frank wouldn’t like it if your fingers are blackened. He probably would have worn those newspaper gloves.
January 22, 2026
🎵I Did It My Way🎵
I went into this knowing nothing about his personal life, so I was surprised at everything, even though I shouldn’t have been. Seems being Sinatra’s friend was simultaneously the best and worst thing that could have happened to you.
I thought this was a very well written book, and the pictures featured were wonderful. I was most interested in his music-making progress, which wasn’t really delved into until the very end—but this wasn’t so much a biography as it was just a glimpse into Sinatra’s way of living.
I went into this knowing nothing about his personal life, so I was surprised at everything, even though I shouldn’t have been. Seems being Sinatra’s friend was simultaneously the best and worst thing that could have happened to you.
I thought this was a very well written book, and the pictures featured were wonderful. I was most interested in his music-making progress, which wasn’t really delved into until the very end—but this wasn’t so much a biography as it was just a glimpse into Sinatra’s way of living.
July 2, 2018
Wow! Picked this up at the library, and loved it. The insight, metaphors, and stories from a fascinating set of friends, family, and co-workers, makes this a fast read. This is a book to read over and over again with lots of pearls of wisdom on how to get the most out of life, and help and encourage others to do the same. The stories of fights, and bad behavior make the telling of his life story more realistic. I'll be buying a copy soon, to read it again and again.
November 27, 2021
This book is great! I'm a huge Sinatra fan. This book gives you an insightful look into the legend that is "ol' blue eyes". It's humorous, deep, thoughtful and loving. I would recommend this book to anyone that wants to learn the style of Sinatra. He had class and taste. Something people today have seem to have lost.
November 19, 2016
Wonderful. The best Sinatra stories from true sources. Words from Frank himself. Love this book, need it on my shelf. A joy to read.
The author wrote and presented the information in a down-to-earth fun way. Respect.
The author wrote and presented the information in a down-to-earth fun way. Respect.
March 5, 2018
A lyrical exploration of what manhood used to be. It was a code of conduct that was self-authenticating and demanding of the best that a man could provide. It is a bracing antidote for the hipster, metrosexual façade that passes for male adult behavior today.
Displaying 1 - 30 of 77 reviews