By Tom Mastronardi

"The story I’m about to relate is true; it really happened, just a few short years ago, before Covid upended the simple everyday pleasure of running into someone you know on the street and having something marvellous happen.

But let’s not bury the lede; you see, I have Gay Talese’s hat.

It all began on a brisk afternoon in March. I was sauntering, possibly whistling – and, knowing myself, likely swanning down Madison Avenue, when I found myself caught off guard, as I believe was the whole of Manhattan, by a sudden, last-of-the-season snow squall.

I pulled my collar closer to protect myself from the fury of the flurry but I was also charmed by the sheer wonder of the onslaught, a sneaky reprise not unlike those extra choruses in a Cole Porter song when he’s being excessively clever.

But that was before my ignominious fall from grace.

I heard my name being called half a heartbeat before I recognised Gay Talese striding uptown. He was sartorially magnificent (of course) and vigorously hailing me.

Mind now, this is Gay Talese, Illustrious Lion of American Literary Journalism, who, even as he approaches ninety, still sports the most immaculate masculine attire­ rakish, resplendent, arguably the style sage of our time.

And he was calling out to me.

Now, I am to no small extent pleased by the fact that I’m seldom intimidated by what anyone else is wearing. I have the confidence and conviction (read: vainglory) that I am the best dressed character in sight. But this was Gay Talese.

“Tom. Tom!” His voice broke through the urban cacophony, and as we met on the sidewalk I extended a well-gloved hand into his even better-gloved one. But Gay was not simply hailing a chance encounter. Rather, you could see vexation in his deep-set eyes.

“Fercrissake, Tom, what are you doing out in this kind of weather without a hat?” There I stood, seriously outgunned, shamefully hatless, snowflakes scattered across what I fancy to be my Werewolf of London hair.

I stammered a feeble excuse (something about not hearing the weather report), vowed to be better prepared, and after a few words of small talk, hied myself hence (hoping that my topcoat, at least, had met with his approval).

It developed, however, that Mr Talese had other plans.

When I returned home that evening, I discovered that my lovely bride had, in the intervening hours, gotten a call from Gay, in which he ratted out my transgression and requested some more viable reason for my lapse.

Now, permit me a brief sidebar; to keep this story accurate, I should mention that the primary (perhaps only) reason that Gay suffers my company is that he has a good degree of partiality to my wife. A good degree.

And considering that he is after all, Gay Talese, (author of Honor Thy Father, Thy Neighbor’s Wife, Frank Sinatra Has A Cold, and much, much more) I find this, if I’m being honest, to be of some concern. I mean, he’s Gay Talese.

“Why wasn't Tom wearing a hat?”

“Doesn't he wear hats?”

“Doesn't he like hats?”

She told Gay that although she really couldn’t explain why I had been foolish enough to venture out without a hat, yes, I did both wear hats and indeed maintained a keen affection for them (notably a lovely trilby purchased while on a recent hop to London).

Beyond that, she went on to say that I had, albeit halfheartedly, been shopping for a new homburg in the waning days of the winter we'd just exited. Or it appeared we were exiting, until this afternoon.

“No.” Gay insisted. “No, no, no.” I wasn't under any circumstances to purchase one; rather I was to be conveyed to his East Side townhouse to be presented with one of his own.

One. Of. His. Own.

A few days later, my better-half and I found ourselves visiting the remarkable home where Gay and his wife, the irrefutably erudite Nan, have lived for 50 years. Once the pleasantries were exchanged, Gay decreed that he and I leave the ladies to chat, and I was ushered up five flights to the sanctum sanctorum that is Gay Talese’s Hat Closet.

I drew a deep breath, and as he followed me in, I could swear I heard the flourish of trumpets; or maybe it was a harp’s glissando.

Yes, there were hats. Four full walls of hats. Hats meticulously positioned upon hooks. Hats of every imaginable sort. Fedoras, trilbys, panamas. An anthology of headgear, to be sure, but also the personal ‘his-story’ of one of NY’s legendary men.

I snapped out of my reverie as Gay popped a black number onto my unworthy head. Removed it. Scanned the walls for another candidate and then tried another one. Rejected it as well.

And then, three being the charm and all, his hands lit upon an absolutely perfect dove grey Borsalino homburg. He put it on my head. Adjusted the brim. After regarding me with an unnervingly critical expression for a moment, pronounced his satisfaction.

Gay’s right. It is an undeniably wonderful hat, and I look good in it. But it’s more than something to keep my head warm in a sudden snowfall. For in the simple generosity of gifting me with this homburg, I feel Gay has validated my place in the continuum of Gentlemen Who Dress Like It Matters.

I feel anointed, somehow, to buck the trend of casual-what-the-$%ck, to carry on with neckties and three-piece suits and casually insouciant accessories. I’m incredibly touched, humbled, and more than anything, left with the feeling that this has been an investiture as much as anything.

Then, just as suddenly as we had whooshed up the stairs, we headed back down, collected my wife, bid Nan goodbye, and left. To dinner. A martini. And then on to Birdland for some seriously stylish swing.

Anyway, that’s how I came to have Gay Talese’s hat.

Which, for the past few years, has left me with a question: Should I wear it, or keep it under glass?

Thoughts?"