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The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin'

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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 intimat 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.


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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 intimat 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.

30 review for The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin'

  1. 5 out of 5

    Steve Kettmann

    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. 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.

  2. 4 out of 5

    Harold

    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. 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.

  3. 5 out of 5

    Andreya

    I love learn about famous people's privent lives! I love learn about famous people's privent lives!

  4. 5 out of 5

    Jess

    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 thos 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.

  5. 4 out of 5

    Dennis Martin

    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 s 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.

  6. 5 out of 5

    Leonardo Etcheto

    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.

  7. 4 out of 5

    David Christensen

    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.

  8. 5 out of 5

    Heather

    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.

  9. 4 out of 5

    Renee

    Matt made me read this before he would marry me. Frank was a stud. I might have a little crush on Frank Sinatra.

  10. 5 out of 5

    Beby

    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. 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.

  11. 4 out of 5

    Nikolas Bayuk

    If you need a guide on how to live your life, this is for you!

  12. 5 out of 5

    Todd

    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 h 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.

  13. 5 out of 5

    Sue Martin

    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. 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.

  14. 4 out of 5

    Elsabe

    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.

  15. 4 out of 5

    Noah Letner

    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.

  16. 5 out of 5

    Matthew Dambro

    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.

  17. 5 out of 5

    Jeff Laporta

    Loved the insight into the daily life of a fascinating person and the many interesting stories.

  18. 4 out of 5

    Sharon

    Really interesting book and well researched. Especially if you really liked F.S. Tells much here that most of us never knew and it was fascinating.

  19. 4 out of 5

    jerry

    Sinatra was a looney.

  20. 4 out of 5

    Rob Pritts

    Swing Baby!

  21. 4 out of 5

    Carlton Moore

    “You know, those were carefree, intelligent, and very stimulating days and nights.”

  22. 5 out of 5

    Lisa

    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.

  23. 4 out of 5

    Tes

    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 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.

  24. 5 out of 5

    Lauren

    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, 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

  25. 5 out of 5

    Terri Lynn

    I will always be a little in love with Frank Sinatra and his music, his acting, and his humanitarian acts and love. This book feeds that love in many ways with very personal recollections from his wives (who all loved him even after the breakups), his adoring children (who he never spanked or abused like Bing Crosby did to his), his friends, ex-loves (who he did not marry) and associates. If you love Frank, you'll like this a lot. I will always be a little in love with Frank Sinatra and his music, his acting, and his humanitarian acts and love. This book feeds that love in many ways with very personal recollections from his wives (who all loved him even after the breakups), his adoring children (who he never spanked or abused like Bing Crosby did to his), his friends, ex-loves (who he did not marry) and associates. If you love Frank, you'll like this a lot.

  26. 5 out of 5

    Vanessa

    I loved the way this book was organized. It was not your typical autobiography, this book was the more random style of Sinatra such as his drink, his hats and philosophy of dress for men, his friendship with the Rat Pack, and his stance on issues during that time in American History. Very fun, interesting read.

  27. 5 out of 5

    Maxine

    Actually one of the better Sinatra books I've read. It is a biography but the chapters are broken out by 'Sinatra Philosophies.' There's a chapter on dress code (I love his style, a real dandy) another chapter on women, family, etc. I have read multiple Sinatra bio's and this one was the first to offer new information I hadn't previously read. Actually one of the better Sinatra books I've read. It is a biography but the chapters are broken out by 'Sinatra Philosophies.' There's a chapter on dress code (I love his style, a real dandy) another chapter on women, family, etc. I have read multiple Sinatra bio's and this one was the first to offer new information I hadn't previously read.

  28. 5 out of 5

    Louis Picone

    Insightful, funny & sometimes silly book (like way too much print dedicated to how Sinatra liked his ice) - I recommend reading the acknowledgements first. The author had pretty good direct access to Sinatra, but this does not always come out in the book which sometimes just seems to be a retread of second hand stories. Good bathroom read as it can be digested a few pages at a time

  29. 5 out of 5

    Lisa

    It took me quite a few pages to get used to the voice of this book, but maybe that was because I was too anxious. This was my first exposure to the details of Frank Sinatra's life. After a while, I settled in and really enjoyed the writing and the pictures. I think have a little crush on Frank now. It took me quite a few pages to get used to the voice of this book, but maybe that was because I was too anxious. This was my first exposure to the details of Frank Sinatra's life. After a while, I settled in and really enjoyed the writing and the pictures. I think have a little crush on Frank now.

  30. 4 out of 5

    Marilyn

    I absolutely loved this book, it is such a fascinating study of the man and his philosophy of life. It was a rare glimpse at the private side of Frank Sinatra and the photographs are just outstanding. There are many stories from friends and family that give us a true sense of the kind of man he really was.

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