How to Dress “My Way”

What does it mean to be a man?  My recent reading has caused me to wonder about this.  I can’t answer the question, I suspect, but I can maybe address one small part of it.  The old cliché that “clothes make the man” holds true.  And also confines us.

Women are lucky.  They may not realize it, but the eternal cry of “I can’t figure out what to wear!” is a cry of victory.  It is a cry men cannot easily make.  We rarely have the difficulty of putting an outfit together, and, while it’s easy to say that this is because we lack the skill or desire to do so, the truth is we don’t get the opportunity.  Our wardrobe choices are very circumscribed.

I rarely pass for someone with good fashion sense, but I do think there are some guidelines.  Men can turn to models.  What is the model of a well-dressed man?  How do we know what is or is not acceptable?  We need look no further than the archetype of a man.  I know, some will say the tough guy like John Wayne, while others will point to the fashion-plates of the day, but I say that if anyone was really a man, it was Frank Sinatra.

Now, I’m even less an expert on Sinatra than I am on fashion, and I’m not especially a fan, but I do know that if he could wear it, then it’s okay to wear.  Sinatra had four looks, which I will address one at a time: black tie, tailored suit, golf clothes and aloha-wear.

Sinatra epitomized wearing the modern tuxedo.  None of this white-tie-and-tails stuff.  That may have worked for Fred Astaire, and might be suitable if invited to the royal wedding, but today’s man dresses formally in a straight black tuxedo with black tie (after midnight the tie may be untied and worn loosely).  Under certain circumstances it is acceptable to wear grey (as in a friend’s wedding party) or off-white (one’s own wedding), but otherwise, black it is.  Those who have musical experience, performing either in an orchestra or choir (I’ve done both), will in fact have a trusty tux.  The rest rent, but it’s something everyone should do at some point.

Now, as a product of the 70’s I am not unaware of the amazing things that happened to the tuxedo during that decade.  Many of us possess an embarrassing prom photo dressed in a tuxedo of some unnatural color such as powder blue or lime green, and I will not apologize for that, nor for the ubiquitous ruffled shirt.  You had to be there, and there was, I confess, something fun about it.  In my closet I had a variety of shirt ruffles in different colors, and sometimes I miss those chances to play crazy dress-up. 

Then there is the sharp suit.  Fashions change slightly, but only so much, and I believe that at some point in his life, every man should own a well-made tailored suit.  The fear of getting dressed up in modern society comes from buying off the rack.  These are indeed not much fun to wear.  A good suit, on the other hand, made to your specifications, is as comfortable as anything you will ever wear.  When Sean Connery first assayed the role of James Bond, director Terrence Young, the epitome of style, took him to his tailor to have a suit made, and then assigned him to sleep in it, in order to become truly comfortable.  The fact is, when wearing a good suit, you feel different, more confident, more…well…manly.  I wish I had more chances to wear mine.

What about the golf outfit?  Okay, I can’t speak to this much, not being a golfer.  I confess I’ve never been any good at it; no matter how much I perfect my form, in the end it always bounces off the door of that damned windmill.  But seriously folks, I do not understand plaid pants and fringed shoes and those weird caps.  But if Sinatra could do it, then it’s good enough for me.

Finally, the aloha shirt.  Not something Sinatra would wear on a regular basis (as, I confess, I do).  But, in the tropics, he was not afraid to be seen in a bright print shirt and a pair of khakis.  The aloha shirt (also known outside of Hawai’i as the Hawaiian shirt) has a long tradition, and there are many forms.  It was a way of adapting Polynesian prints to what was considered more “modest” dress. 

Some vintage shirts can sell for hundreds of dollars, and even newly made “vintage” shirts can be quite pricey.  The styles range from bright floral patterns all the way down to muted prints.  Generally speaking, the brighter the print, the more likely the wearer is a tourist.  Locals will wear aloha shirts, but they will tend to be subdued, reserving the brighter prints for more formal occasions such as weddings.  Yes, aloha wear is dress-up in Hawai’i.  You will routinely see businessmen wearing a tasteful shirt and nice slacks.  If it’s tucked in, he’s dressed for serious business; the rest of the time the shirt is worn untucked.  No man in these places feels the least bit self-conscious.  Nor should he.  It’s the closest he will come to having the fun wardrobe choices women take for granted.  My own closet is full of aloha shirts; I can wear a different one to each class session of the semester and never repeat.  What does that say about me?

So there you have it: how to dress like a man.  If this is all you have in your closet, you’re good to go.  Maybe as a man my choices in dress are limited, but even so, I can do it “My Way.”


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