MMD October 22, 2014 0

Frank Sinatra, amongst other things, was one of the sharpest dressed men of all time. Back then, looking good had nothing to do with Ed Hardy and fashion was something the “Chairman of the Board” took very seriously. It’s rumored that he once kicked a guy out of a party because he wore a brown suit at night. That was a big no-no for Old Blue Eyes. If it was nighttime the color of choice was black. And to Frank, the importance of getting dressed up couldn’t be overstated.

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.”


For Frank Sinatra, as was the case with many men of his generation, the Fedora was an integral part of his wardrobe. He wore it proudly. It’s a fashion that unfortunately, for whatever reason, didn’t stand the test of time. I attribute that to a lack of formality in today’s society but remember, there’s no law against still wearing a fedora.

Frank Sinatra on hats: “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.”

The Chairman of the Board probably had some of the finest tailored suits in the world. His thoughts on suits were as follows, “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.”

As for the shoes that went with the suit, “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.”

When it comes to suits, there’s a lot involved, Frank even had rules for those little finishing touches that define a well-dressed man: “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.” “Shine your shoes.” “A pocket handkerchief is essential, but it needs to be perfectly folded.” If you really want to dress the part of Sinatra his pocket squares were usually orange, his favorite color because he thought it was “the happiest color.”


Frank even had some words of advice for you less than tidy gentleman:

“Having messy closets is like putting on clean clothes over dirty underwear.”

Once you’re out on the town, you’re looking good, feeling good with two fingers of Jack in your glass, it’s important that you stay looking good so if anybody should touch your carefully put together ensemble tell them what Frank Sinatra would have told them, “Take your hand off the suit, creep.”


Text and quotes taken from The Way You Wear Your Hat by Bill Zehme

Article By: Jon DaBove

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