The Well-Dressed-Gentleman of New York

Submitted into Contest #145 in response to: Write about a character who decides to give themselves, or someone else, a fashion makeover.... view prompt

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Coming of Age

The first time I saw the Well-Dressed-Gentleman, he was just walking, no, strolling down St. Marks wearing this perfectly creased three-piece-charcoal-gray-suit, bowler hat, and an umbrella (it was not raining). There was a silver pocket watch and fob on his vest, and his black wingtips were buffed to an immaculate shine, reflecting the afternoon sun as they made a rhythmic click-clack-click-clack on the pavement, and his umbrella dangled languidly from the crook of his elbow as his hand rested in the pocket of his suit jacket and the other hand held up an old and well-worn book. Needless to say, the hand was gloved.

I didn’t see the Well-Dressed-Man’s face at all. 

Thing was, I only saw him for, like, a second or two before he turned a corner and disappeared. My immediate instinct was to follow him, but I thought better of it, cause, ya know, I don’t have a dungeon/torture room in my basement. I don’t even have a basement, cause, I mean, who can afford a basement in New York? Anyway, you get my point. I’m not some creepy stalker-guy. I know I kinda come off like one in this story, but I promise you, I’m not, even though that is probably exactly what a creepy stalker guy would say.

Anyway, the Well-Dressed-Gentleman turned the corner in a jaunty fashion and, just like that, he was gone.

And I was sad.

I don’t know why. At least, I didn’t at the time. But I was suddenly very sad, which wasn’t really anything new. I’m kinda low-key sad most of the time. Melancholic one might say, if one were a 19th century dilettante.

 I saw him again in Central Park on a Saturday. He was walking, no, strolling along the lake, this time with a polished black cane, a black long coat (it was July), and a black fedora. He looked like a perfect silhouette, tall and lanky, sans the pocket watch and fob, gold this time, dangling from his vest, and his bright red tie. 

Again, I did not get a good look at his face, but I knew it was him, not just from his shape or the way he moved, though both were incredibly distinct, but the way his clothes hung off of him, as if they were living extensions of his body.  The swish of the long coat behind him was like a cat’s tail.

So obviously, I found myself staring. Again. But this time he looked back at me.  But I still didn’t see his face, because I immediately looked away and kept looking away until the click-clacking of his shined black shoes faded in the distance.

Once more, I was taken with a sense of melancholy.  Once more, I didn’t know why. Or at least I couldn’t articulate it. 

Then I saw him again. It was winter. There was snow. Fresh, white, shimmering snow against an inky black sky. And so, as a matter of course, I found myself in my favorite café/bar (at least my favorite when it’s winter and there’s fresh white snow against an inky black sky; I also have a favorite café/bar for Fall and Summer, respectively).  

The place was sparse, dimly lit, and quiet, and every now and again I saw the shadowy flicker of mice scurrying along the wall out of the corner of my eye.  Then he walked, no strolled in. He wore a wool coat (black), and a cream-colored scarf over yet another three-piece suit, this one a deep crimson with pinstripes, and a pair of shined red oxfords to match. The pocket watch he chose for today was neither silver nor gold but bejeweled in an ornate pattern like a tiny mosaic. His hat was a beret this time (also black). 

He sat on the couch opposite me, by the fireplace, and I saw his face. Not his eyes, though.  His eyes were hidden by a pair of round wireframe sunglasses that reflected the flames of the fire, creating a somewhat demonic look. Now, contrary to what you might expect, he was not an especially handsome individual.  Not ugly either. I mean… he was almost handsome, but his face was just a bit too long, his chin a touch to sharp, what he was was interesting looking.  Perhaps that’s why he dressed the way he did.

He was pale. Very pale, which was only accentuated by the deep red and black of his clothing. As I took him in, I had completely forgotten that I was staring at him, and I was surprised to find him looking back at me. More surprised still that I didn’t look away this time. In fact, I nodded. My nod was returned. 

Now what? 

Neither of us looked away and went back to their business, which would have been the natural thing to do in such a situation. It was like a game of chicken now.  Had he recognized me from before the way I recognized him? I didn’t know. I still don’t know.

As he looked at me, I was suddenly struck by a crushing wave of self-consciousness. Surely, this man, this living silhouette, this Well-Dressed-Gentleman who stood before me,  surely he must have been sizing me up behind those green tinted glasses, starting with my barely-held-together sneakers with the flapping soles, soaking wet from the slush and snow, working his way up to my frayed ill-fitting blue jeans, and finally my stained T-shirt with the holes along the stretched out collar and faded threadbare jacket. Surely this man, this Well-Dressed-Gentleman of New York, was judging me, me and my complete and utter lack of care, effort, or concern. Judging me and my slouched beanbag posture.

I could only imagine the sheer unfiltered contempt in his hidden eyes.

Still, for whatever reason, I didn’t look away. I held the gaze.

Let him judge. 

Eventually, the moment passed. I sipped my drink (a dark stout) and he sipped his (a port), and we read our respective books. I was reading a book of short stories by one of my favorite authors, all of which I had read many times before, and he was reading the same well-worn old book I saw him reading back in the Spring. I glanced at the cover: Leaves of Grass.  We made periodic eye contact, followed by nods acknowledging one another’s presence, then we went back to sipping and reading as the fire crackled and the mice scurried along the shadows.

Then the Well-Dressed-Gentleman got up. I looked at him. He didn’t move, didn’t leave, just stood there. I soon realized that he was waiting.  For me. I stood up.  The Gentleman didn’t wait any longer, but walked out the door. I followed.

It was snowing and fat fluffy wet snowflakes clung to me as I followed the Gentlemen, who kept a steady pace, five or six feet in front of me.  Neither of us spoke, but just walked, me and this dark silhouette, like a shadow, moving through a twisting pitch-black tunnel of brick, wind, and snow, throwing only the slightest backward glance in my direction every now and again, not even breaking his stride.  He turned a corner, ducking into an alleyway.

Here I stopped. 

I peered in and saw the Well-Dressed-Gentleman standing about twenty feet off, illuminated only by the faintest glow of the streetlight behind me and the white glow of the full moon above, half bathed in darkness, his perfectly round sunglasses glinting.  For the life of me, I don’t know what possessed me to ignore every ounce of common sense and self-preservation and follow him into that alleyway, but follow him I did, lowering my head and shouldering through the bitter howling blast of the concrete wind-tunnel.  I followed him around another corner, and another, and another as we made our way down the twisting urban labyrinth, till we came to a rusted metal gate, covered in ivy.

The Well-Dressed-Gentleman fished in his deep pocket and produced a long thin skeleton key. He unlocked the gate and opened it with a long, painful crrrreeeaaaak that shot through my ears and set my teeth grinding.  Then, saying not a word, the Well-Dressed-Gentleman slipped through the gate of the back entrance (to what I did not know). I hesitated, but followed, making my way through an immense garden of dead and gnarled plants covered in snow, which made them look like strange abstract sculptures. This was the first time in my impromptu journey that I took my eyes off the Gentlemen, lost in the surrealness of where I was and what I was doing.

SLAM!!!

I immediately whirled around and saw the Well-Dressed-Gentleman standing by an open cellar door. He then opened the second cellar door and let it drop.

SLAM!!!

He stooped low as he went down the cellar.

For a third time I hesitated, thinking to myself: “Is this how I’m going to die?”

I mean, that was a distinct possibility, was it not?

But for reasons that to this day remain unclear…. yeah, I went down that cellar in that strange back-alley garden in Greenwich. You’re Goddamn right I did.

As I walked down the dark, narrow stairway, towards an old green wooden door, I heard the muffled sound of… violin music.  I reached the bottom of the stairway. The doorknob was an antique, glass with an ornate design, and felt cool in my hand. 

Now as I turned that knob, I can’t say for sure exactly what I was expecting to find on the other side of that door. Could’ve been any number of things, really: torture room, fight club, sex cult, society of vampires, Christian fundamentalists, etc. But one thing I was absolutely not expecting to find was a secret underground fashion boutique.

Much like the Tardis, it was bigger inside. 

The cavernous underground room stretched on for what had to have been several city blocks. There was an immense fireplace, gilded lantern sconces on the walls, Victorian molding along the ceiling and hardwood floors, highbacked crimson leather armchairs, dark green walls, and a high, high ceiling. And clothes.  So many clothes; men’s and women’s clothes draped on antique department store mannequins in all manner of casual poses; suits, tuxedos, blazers, cocktail dresses, swing dresses, trench coats, leather gloves, high boots, pill box hats, scarves, shawls, wraps, vests, and vales; tweed, wool, cloth, and corduroy; trousers, chinos, jodhpurs, and capri’s; Oxfords, Derby’s, Loafers, and straps; florals and sequins and slips, and on and on and on and on, all lovingly, immaculately, painstakingly tailored, sewn, and cut; an elegant drawing room soiree frozen in time. Oh, and that violin music I mentioned earlier, that wasn’t a recording played on a Victrola (which would have been in keeping with the overall vibe of the place), but a violinist in a sleek black evening gown standing off in the corner.

I suddenly jumped when I saw a ruffle of movement out of the corner of my eye only to realize that mingling amongst the wooden mannequins were other people, all dressed to the nines, many swirling drinks in their hands, walking, no, strolling down the aisles of clothing on display, lovingly caressing the material. Some were dancing, slow and close, all around me, smiling pleasantly. I admit that, for a moment or two, I had to ask myself if this was an Overlook Hotel type of scenario. It was all so surreal, yet all so comforting and joyful.  

And the Well-Dressed-Gentleman? I had forgotten all about him until he stepped forward, as if out of thin air, smiling now. More than ever, I felt deeply, glaringly inadequate. What was I, but a blight on the beauty and elegance of that room and those people? And those clothes.  Those divine and glorious clothes. I wanted to disappear, but I stood frozen as the Well-Dressed-Gentleman of New York stood before me and removed his tinted glasses. His eyes were as pale as his face, gray and sad, like an overcast sky.  

He placed a slender, delicate hand on my shoulder and said, “Welcome, my friend. I can see that you are kindred spirit.”

I was surprised to find that his voice was a rich baritone that didn’t quite match his face or frame. Everything about the Gentleman was just a bit incongruous. Yet this made him no less appealing. If anything, it made him more so.

I glanced down at my clothes (if they could even be called that), embarrassed.  The Gentleman smiled warmly and gently guided me through the maze of vintage clothes, down a hallway, and through a large set of double doors into a great circular room of dark oak with a Cheval mirror in the center. Wrapped around me were more clothes, just as beautiful as the ones adorning the mannequins in the front room, clothes of every conceivable style, design, vintage, and combination, with row after row of shoes to match, a glass cabinet display of pocket watches, and dressers stocked with smoothest socks I’ve ever felt.

 I turned to the Well-Dressed-Gentleman, who stood at attention, holding his beret. It was the first time I had seen him without a hat and so the first time I noticed that his hair was completely white, the very color of the fresh fallen snow outside, and for the life me, I could not guess at how old he was. In fact, I’d say he was…. ageless.

“Please,” said the Gentleman. “Do take your time.”

I smiled, still embarrassed, and told the Gentleman: “Thank you. But I couldn’t possibly pay for any of this.”

The Gentleman’s smile widened and his eyes gleamed. “Oh but you misunderstand, my friend.”

“I do?” I said.

“This is not a store.”

“It isn’t?” I said.

The Gentleman shook his head with a chuckle. “No. This is my private collection.”

“You’re joking,” I said.

“Not a bit of it,” said the Gentleman. “You see, I much prefer to share my darlings that they may live and breathe than horde them away in a dark closet in which to collect dust and be eaten by moths. You will join us in the ballroom, will you not?”

“Ballroom?” I repeated.

Again, the Gentleman chuckled. “Find something that speaks to you. Something that calls to you.”

With that, he left me alone with the clothes.

Something that spoke and called to me? I shrugged and began my search.

I’ve never much liked clothes shopping, nor particularly cared about what I pulled from the rack, and so one might think that the situation I found myself in would have found me standing frozen and gawking. But I wasn’t in that massive closet a second before something did indeed call to me.  I snatched up a bright red dress shirt, and a black jacket, vest, and slacks, along with a black leather belt with a gold buckle and a blindingly shiny pair of black oxford shoes.

I inspected myself in the mirror for a moment before removing the jacket and returning it to the rack from whence it came. 

I looked at myself again, appraisingly. Yes. Yes, this was more like it. 

This was more like.

May 14, 2022 03:14

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2 comments

Erich Cliffe
17:39 May 19, 2022

1. I'm enchanted. 2. I ache to browse the Well Dressed Gentleman's private collection. 3. I may be infatuated with the Well Dressed Gentleman.

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Nick Izzo
02:48 May 20, 2022

Thank you so much!

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