I have nothing in common with Frank Sinatra. But I would like to. I would love to have twinkling blue eyes, or a great singing voice, or what was rumored to be a huge… ego.

But I am without. So the way I look at it, the closest I can get to Frank is his fashion sense, more specifically, the fedora. That quintessential symbol of classic Hollywood mansomeness. An item that compliments every ensemble, be it a perfectly tailored suit, or your girlfriend and nothing else.

Unfortunately, like most classic, brilliant, once-awesomely-sharp trends, that slick style of the ’40s and ’50s has been tainted by . . . the douche. For years I have been fedora shopping, trying on hundreds of hats, all of which quickly fly back on the shelf for fear that I look like Wilmer Valderrama.

I know: Style is about self-expression and shouldn’t be dictated by other’s opinions. But it’s too late. My own personal toolbag alarm goes into overdrive every time that hat hits my head. You know who can pull off fedoras? Old men and Taye Diggs. That’s it! Steve Martin is photographed constantly with an array of fedoras and he looks cooler than anyone in the room. Cut to Criss Angel, and all is lost.

Even Pharrell knew better than to wear a proper fedora a few years back, when he busted out that Smokey The Bear rig at the Grammys. And I totally get that. If I were a huge, trend-setting celeb, I would test my influence by wearing the most ridiculous hats known to man. I would arrive on red carpets wearing a three-point pirate hat unironically and see if the kids follow suit. Or a maybe a mining helmet, or a large-billed Sandlot-style baseball cap, just to see how quickly it catches on and dies out.

If Frank were around today, he would be really old. But he would also hang his head in shame as he scooted by the nearest lounge and witnessed his beloved, classic fedora being worn by guys who think a Highball is a baseball term.

See, most guy can’t wear really it with any old T-shirt and jeans. You’ve gotta have a classy ensemble to match, just like Frank did. Witness the natty sportcoat, tie and pocket square at the top of this page, for example. So the next time you go shopping and you place that classic hat on your skull, take a good look in the mirror and consider this: Are you truly worthy of the fedora, or should you just settle for a hoodie?

Photo: Getty Images/The LIFE Images Collection