Sinatra Style

Sinatra had an impeccable sense of personal style, which in turn influenced his generation. He said:
“For me, a tuxedo is a way of life. When an invitation says black tie optional, it is always safer to wear black tie. My basic rules are to have shirt cuffs extended half an inch from the jacket sleeve. Trousers should break just above the shoe. Try not to sit down because it wrinkles the pants. If you have to sit, don’t cross your legs. Pocket handkerchiefs are optional, but I always wear one, usually orange, since orange is my favorite color. Shine your Mary Janes on the underside of a couch cushion.”    Text excerpted from, and in turn from The Way You Wear Your Hat, by Bill Zehme

Sinatra’s Style Rules

  • It takes two hands to put on a hat the right way: Back brim curled up, front tugged down to a couple of inches above the right brow.
  • Never wear brown at night. Never.
  • There’s no excuse for brown shoes past sundown…. Or white shoes. Or anything gray, unless it’s deep charcoal. Or blue, unless it’s midnight blue. In fact, let’s keep it simple: after dark, men should wear black.
  • Ties should be silk. And conservative.
  • Cuff links always. But leave the fancy jewelry to Sammy.
  • When dressing formally, a vest is better than a cummerbund.
  • Don’t wear a tuxedo on Sunday.
  • Having messy closets is like putting on clean clothes over dirty underwear.
  • The shower is a great place to steam out the wrinkles in your dinner jacket.
  • Orange is the happiest color.
  • Don’t hide your scars. They make you who you are.
  • When it comes to pockets, everything should have its own place.
  • A pocket handkerchief is essential, but it needs to be perfectly folded.
  • Shine your shoes.
  • Nails: Trim. Buff. Clean.
  • Take your hand off the suit, creep.

What’s a Guy Gotta Do to Get Some Respect!?!

You really want to know?

It that’s not a Rodney Dangerfield line, we’ll try to give you a straight answer.

One of the greatest things about America is that we have no permanent aristocracy.  Seriously. A guy named De Tocqueville remarked on this, on a tour of America, that virtually every citizen he met believed he could better himself.  Few of us felt limited to a low rung on the ladder of society just ’cause we came from a poor or rough place.  It just took hard work, a code of honor, and guts.  Until the whiney, entitlement era, most men got this fact. By the millions, it’s how our ancestors built the good ‘ol USA into the greatest nation on earth.  Many years after De Tocqueville, like most of the Rat Pack, Sinatra emerged as a self-made man.  So too, did many of the leaders in America today, from all walks of life. For the Chairmen, these are examples of this can-do attitude.

We can learn from these men.  Just as Washington, at an early age, famously wrote down a book of rules of behavior for himself which became a popular volume for children in later years, self help books, organizations and websites are immensely popular today.  Even in WWII, one of the most requested books by common GIs was… Emily Post’s Rules of Etiquette–!  Imagine that: Soldiers sitting in foxholes would write home and ask for this as their #1 request, reading how to straighten up and fly right.  Amazing.

One of our functions as Chairmen is to give each other good advice on becoming the best we can be.  Here’s an example.  Feel free to add your suggestions to the blog and comments section of this website.

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