Book Talk: The Way You Wear Your Hat

“He once said ‘I think my real ambition is to pass on to others what I know’…it occurred to me that he hadn’t made good on his promise. Men had gone soft and needed help, needed a leader, needed Frank Sinatra. This book was created not so much to report what Frank Sinatra has done but to celebrate how he did things and how he reacted to moments most human. It is part biography of sensibility, part handbook for dreamers of large dreams.”


“The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin'” by Bill Zehme (1997)


Discovery. I always say that I envy someone when they watch one of my favourite films for the first time. I lament that never again will I be able to experience certain movies, music or books as brand new. This brings to mind the time when I was first exploring the world of Sinatra & Friends, learning about vintage media and all things swank and swinging. I’m happy to say that the first books I ever bought to help me understand FS and his world were bang-on perfect. His life – Behind the Legend. His music – The Song is You. The Rat Pack – Shawn Levy’s Rat Pack Confidential. And for Sinatra’s style – how to live and cavort like the Chairman – there is no better place to start than where I did, with the book we’re looking at today. The Way You Wear Your Hat is nothing less than a manual, a text book, a how-to book. Wanna know how many mints to keep in your pocket – how many, what kind and what pocket? – it’s all here.

Bill Zehme is a noted author who has published books on Andy Kaufman, Hugh Hefner and Regis Philbin. This his text book on Sinatra’s swank style he has broken up into chapters each relating to a special element of livin’. In the “Wee Small” chapter, Bill reports on the Chairman after dark and notes that Sinatra – like Presley – hated to be alone. FS needed many around him and all were required to stay up as late as he did. Zehme says that many of the people he interviewed, when they became exhausted, would say they were going to the bathroom and head off to bed. The author introduces the “maestro of matters wet”, Jackie Gleason, and describes the Great One introducing Frank to one Jack Daniel’s and shepherding him through his first real bender in the 1940’s. I always thought it was cool that Frank favoured Jack throughout his life as I had grown up associating the sour mash with decadent rock stars. Zehme adds that Sammy Davis desecrated the liquor by mixing it with Coke and that the distillery dedicated an acre of its land to Sinatra its celebrated patron.

Frank and Jackie with Toots Shor.

Zehme details night life at Toots Shor’s on E 51st St. and offers a drink-by-drink account of how Sinatra would spend his time at Jilly’s. No matter how much “gasoline” he consumed, Frank apparently never loosened his tie or undid a button in public.

In “Ring-a-Ding-Ding”, Zehme discourses on Frank’s adventures with his gang and issues a detailed guide to the lingo the group adopted. “I think it’s going to rain” meant that they were about to blow the scene as too many “clydes” had spoiled the atmosphere. In “Pallies”, we learn the key to Frank’s relationship with Dean Martin and it is confirmed that Dino was not the lush he pretended to be. Zehme details the origins of the Holmby Hills Rat Pack and shares stories of Sinatra intimates like pianist Bill Miller. The Millers had been asleep when the reservoir behind their Burbank home burst. Their house had been inundated with “ungodly furies of water”. Bill and his daughter survived but his wife perished. FS had to identify Mrs. Miller’s body – “it’s a picture I can’t get outta my head” – and paid all hospital and recovery bills. Like Judy Garland. It was the late Sixties and Judy was constantly struggling. Tony Bennett got a distress call from her saying she was being attacked in her room at the St. Regis Hotel. Bennett panicked and called the first person he could think of. Police? Sinatra. Judy called Bennett back 12 minutes later; “I ask for help – and now I have five Jewish lawyers in my room and four hundred police out in the street!. Like Sammy Davis. Frank’s support of his friend – moral and financial – was key to getting Davis back on his dancing feet, emotionally and professionally, after the wreck that cost him his eye. In “Drinking Again”, we learn of Frank’s insistence that he himself and those around him must know “when to knock it off”. Zehme details the bacchanal of the Vegas stage shows and the many drinking “rules” including the number of ice cubes required in a cocktail and in which hand Frank would hold his drink. Chazz Palminteri relates a story of the significance of sharing an olive with the Chairman. Cigarettes and smoking are also discussed.

The fellas; Tony Curtis, Nat Cole, Peter Lawford and the Chairman.

In “Style”, we learn about Frank’s celebrated hats and the colour he never wore at night. Zehme says that FS “equipped his pockets with precision” and gets detailed about their contents (including only hundred dollar bills, 20 of them and no coins). The rules for evening dress are shared including the best way to shine your “mary janes”.

But The Way You Wear Your Hat is not all frivolity. The reader will detect a definite change in tone when the topics turn in the later chapters to “Broads”, “Love & Marriage” and “My Way”. Zehme gets serious when he talks of Sinatra’s marriages and his children. Frank is quoted honestly assessing some of his failings and his hopes that part of his legacy is how to not do some things. This change in tone adds a real sincere quality to the book and you will find you almost have two separate stories; one laying out Sinatra’s style and his endless pursuit of ring-a-ding-ding and the other talking about things of much more consequence like family and friends, business, race, who, when and how to fight adversaries real or imagined, maintaining your character and leaving something lasting behind. There’s an added poignancy in that The Way You Wear Your Hat was published a mere six months before Sinatra’s passing.

Some anecdotes; the new doctor Frank went to who he decided was not for him (a bottle of Jack every day?!), pally Dino calling the cops on his own party, Frank has interesting competition when it comes to being LA’s biggest tipper and much more.

All this adds up to a singular book that is great fun with the addition of dialling in with more consequence to the heavier things of life. The result is perhaps the definitive work of required reading for those of us who want to do life Sinatra’s way.

12 comments

      • Nearly. It does more than that. So after you have installed it, you select your local library, and enter your library card information, or if you don’t have one already, sign up for the library card. Then right on the app, you can check out your local librarie E-book collection and audiobook collection, right on your phone, tablet, ipad, without having to go directly to the library and physically checking out the book. It allows you to have your libraries book collection right at your finger tips, not it is a library check out, so you can only have it for a limited time, like two weeks, and they only have so many copies, so you have to wait your turn like you would at the library. It basically just brings your library to your home device instead of going there. Now each local library is different, majority now use Libby, but some are still using overdrive. I would just pop onto your local library website and see what they use or give them a call. Like I said MOST now use Libby but some use other e-platforms. It is definitely worth looking into. You can get many library book reads that way. I use them a whole ton. I check out a book on Libby, and get it sent right to my kindle app, I read it, and then return it when I am done. Love it!

      • I like the sounds of this. Mostly because sometimes a book will interest me, I’ll hunt it down, buy it, have it shipped to me, read it and it’s ok but not great. Now I’ve worked hard and spent money for a book that is meh. I could use the library to test drive books; if I like it, seek it out and buy it. Thanks for the info!

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