I don’t know where the fuck I am half the time. I woke up here one day thinking I was in London. I’m coming from Australia and went to Paris for literally forty-eight hours just to change clothes. So this is where my confusion is now; do I take everything I may need for my next trip, or do I get to come back home before going away again? When you’re cross-dressing, what does one take?

I take the basic things that I wear everyday when I’m not working: T-shirts, jeans, a couple of cardigans and a good few pairs of shoes. I take more shoes than I should – sometimes I travel with ten to fifteen pairs. Mostly men’s shoes, and a few women’s shoes with a heel just in case I need them for TV. I always carry a black suit: I can dress it up or down. If I’m travelling between New York and Paris, I don’t take underwear and T-shirts because I keep doubles in both places, but sometimes I get really upset and freak out that I don’t have the shoes I need for an outfit.

My on- and off-duty persona is a combination of many things; it depends on what the duty is. If I’m doing TV, it depends on what my spirit is work-wise. For the 2016 Oscars, my outfit consisted of one-two-three different designers. I had a beaded bag that said ‘Queen of Fucking Everything,’ which was given to me. I wore a jacket from 1994 that I cut short and wore over a shirt from 2007, and a tulle and ostrich feather skirt over black sequin sweatpants. I just threw it all together. The skirt and the pants were from one designer, the shoes were Marc Jacobs, the jacket was from Mr Kim, a tailor in Korea, and the shirt was from another tailor in Thailand: I had it made when I was working there. And to another more recent event in Savannah with Carolina Herrera, I wore an old Marc Jacobs jacket, and I made this diaper skirt, like a harem pant, in satin chiffon. The fabric came from the donation closet at the Savannah College of Art and Design; designers often donate to them so when I’m there I’ll just go see what they have. Whatever they’re not using, I’ll just pull a few yards from. I wore the outfit with wing tipped, lace-up and suede Marc Jacobs shoes that I’ve worn twice before. Once for my boyfriend’s sister’s wedding, and then again for a fashion week event. I also wore a Tom Ford YSL clutch, and a scarf I made out of scraps of fabric. I had my hair in cornrows, so I just brushed it out. Everyone thought I was wearing a wig, but it was all my hair. This is the look. It’s an androgynous moment in hot-ass Savannah.

Marc Jacobs has been ever so generous with me over the past ten years. I’ve known him nearly all my life, and Robert Duffy who was the ex-CEO of the company too. So whenever I needed anything, and even when I didn’t need anything, they’d send me things. They told me that I’m the only person that they know that sends things back, but I don’t want to be greedy so if I’m not going to wear something I give it back. Good clothing should never be thrown away: you can always cut it apart and make something new with it.

I taught myself how to sew because when I was much younger, I couldn’t afford to buy designer clothes. I grew up in New York City, in the Bronx. I’m number seven of ten kids so I’d get my brothers’ hand-me-down clothes. There was Ronald, Stephen, Stanley and myself. We all went to the same school, and I didn’t want kids to make fun of me so I’d create something different. I would make the pants shorter, fringe the jeans, cut holes into a peace sign, take the collars off the shirts and make them short sleeved. Once a girl called Jennifer Brown showed me how to make a men’s suit with a pattern, but apart from that I taught myself by trial and error.

When I was twenty-three, I was working at Bergdorf Goodman in the city and some girls took me to Studio 54 for the first time. I realised that they only let people in who were dressed outrageous. So I did the same: I wore a crazy outfit, and they’d let me in. I would make a skirt out of tulle and wear it over a pair of tights and cowboy boots before I graduated to heels and then a T-shirt made with a ruffle collar. I’d do something crazy with my hair, and that was this outrageousness. As it got into the late Eighties and Nineties I discovered a shoe store on 14th Street and another on 35th Street called Tall Girls that made shoes for tall women. I’d get my heels from that store. I didn’t think about whether they were used to men coming in the store; it wasn’t important. I just went to get what I needed. ‘Do you have these in a size 13? Thank you, I’ll buy them, done.’

The rest of the week, I would wear no make-up and no heels. But I still made my own clothes. I would make duster coats, almost like bathrobes. I was very heavily influenced by the Japanese: big shapes, a coat that flowed at the bottom and was belted at the waist. I would make a tank top and a pair of loose pants to go with. It’s really funny, I just looked at something that I made back in 1984 and thought, ‘Oh my god, I should redo that outfit.’ Oh yes, people looked at me then, but I never thought I was being provocative. I was just wearing a maxi coat, loose pants and a tank top. For me, provocative would have been the high heels – during the daytime that is – and being in make-up and drag.

I had a friend called Michael Stein. Michael Stein was like the black Divine. He was 300 lbs, with alopecia so no hair anywhere. He would borrow clothing from the stores, hide the price tags and then take them back after he’d worn them. I was creating the clothes at home and eventually I started going to clubs in full drag. I was looking at magazines, trying to re-create whole looks from the catwalk or from ad campaigns. When I went out on the weekends, which was usually on Fridays and Saturdays and sometimes on Sundays, we would get dressed up together because I got into the clubs for free and I would be able to bring in a friend for free. I’d come to the city from the Bronx with all my stuff, my garment bag, my make-up bag, and get ready in a friend’s dormitory and then go with them to the club. After the club I’d go back to my friend’s place, get out of drag and get a train back to the Bronx at four or five o’clock in the morning. Then I became more daring. In the wintertime I would put half of my drag clothes on under a long winter coat and carry the other part in a garment bag. I’d take the bus from Castle Avenue in the projects to the subway. I’d put make-up on on the train. I would get off the train at 125th Street and get the express train, next stop was 86th Street, then 59th Street. I would get off there, get a taxi and do a quick change in the back of the cab so I would get out in front of Studio 54, like, ‘I just arrived – in a taxi!’

Sometimes I would get harassed by a bunch of boys from under the tunnel or over the bridge, you know, ‘That’s a guy, that’s a dude!’ and I’d be like, ‘Oh fuck off’ and keep on walking. I am 6ft4 or 6ft7 in heels, and I’d walk down the street with elegance, such elegance walking down that street darling, feeling fabulous. I never got tapped, never, ever, ever, no one came at me because I was ready and I was up in their face. Or you’d get men who was attracted to it.

My sister saw me for the first time doing the catwalk in a club; I was a bride I believe. She was like, ‘Oh.’ But my brother and sisters and mother all had their own lives. To them I was just their crazy-ass brother. If they went with me, they’d get into clubs that they could never get in to otherwise, you see. I would get there and people would open up like the Red Sea. I was just going right in saying, ‘They’re with me.’ And I’d sashay on in, hang up my coat and have my ball gown on.

I was looking at magazines, at Women’s Wear Daily, at Elsa Klensch. Elsa Klensch was like The Bible. I would look at all those small pictures in the catwalk reports of the models walking the runway in their outfits and I’d try to create that silhouette. It was just insane. I started imitating the make-up. The more I got into it, the more the make-up changed, the outrageous became more pretty, more feminine, more soft. It became more drag than outrageous. I would get inspired by looking at the models in the magazines and want to do that make-up or that look like, ‘Oh my god did you see that Oscar de la Renta ball gown? Did you see that Saint Laurent look? Did you see Mounia? Did you see Katoucha? She looked fierce!’ I would imitate those looks and the make-up, using my grandmother’s sewing machine to create the looks.

Then I decided I wanted to be more like a socialite woman who goes to the Met Gala, wearing ball gowns from Oscar de la Renta, Bill Blass, Saint Laurent, Givenchy, Valentino. I wanted to have that ball gown on, I wanted to be fierce, I wanted to be fabulous. Like, ‘Girl, this is so-and-so from Park Avenue.’ I loved the luxury of it. The luxe. Those women would get out of their limousines and go up that staircase to the Met. When I finally started going to the Met, to the after party, me and my woman Glenda would go together. I’d make my gown, make her gown and we’d go. She was a real girl and I wasn’t but I made myself look like one. You could buy tickets to the party then. This was before Anna Wintour took over and decided, ‘You can’t come, you can come, but you can’t come.’ You could buy two tickets to the after-party for $125 dollars I think.

The first time I went up that staircase I thought I was one of those women. I wore an outfit by David Lee: he made me this black satin opera coat, big, huge sleeves, to the floor. There was this fitted dress underneath it, with a trumpeted bottom. He made me stand while he painted a design on it. So I stood there with my arms out, losing blood as he was painting on it. Then he applied all the stones, and made a big huge bow and matching gloves. I remember I showed up with big pink fuschia frosted lips and black and silver smoked winged eyes, my hair done in a French twist with a big bow. I showed up and I thought I was… it was all about me at that point. It was winter and the wind was blowing in my eyes, it was so cold. But feeling that wind blowing me up the steps – whoosh! – holding me up. Fantabulous honey, fantastic, just fabulous.

The people, they would just look at me, just look at me. And I would look back at the people I’d seen in the magazines. I saw this really handsome guy – I’d seen him in pictures and thought he was so sexy – and I remember seeing him leave the dinner with Diana Ross. I would show up at the museum and I was standing at the entrance of the main hall of the Met watching people coming out of the dinner and either going out of the building to another party or going to the after party. That was my catwalk. I would walk down that long, long, long corridor with the mummies, and people looked at me, thinking I was crazy. All the snobbish Upper East Side women with their designer ball gowns and their diamonds and their jewellery. Watching the celebrities come out of the dinner was fantastic to me, and we’d go dance and have a wonderful time and I’d think I was a rich white woman.

A few years later, I moved to Japan for what was meant to be two months but became almost three years. I hung around with the Elite modelling agency, they’d host parties and I’d be invited to go. I would get dressed up and go thinking I was one of the models they were booking: Iman, all these girls. My style of dressing changed: I became more fashionable. The girls were wearing jersey leggings, flat shoes or ankle boots and an Azzadine Alaïa jacket or a big overcoat to castings, and I would make my own version of that. I would get a piece of wool, cut it the shape that I wanted, put elastic into the waist to get a peplum waist and make a dolman sleeve. I made this big leather bag and wore it with a black turtleneck and a black scarf at my neck and these cheap $50 black suede pussy boots that I got from 40th Street. That was my look. I would imitate those girls. People would say, ‘You’re so androgynous,’ and I’d say, ‘Yes I know,’ with my hair out, blowing in the wind, feeling that moment.

At one point I did feel like an outsider because I wanted to be a part of that group but I couldn’t afford it. I couldn’t go to Biarritz, I couldn’t go to Gstaad, I couldn’t go to St. Barts or to the places where rich people go to have fabulous luncheons and dinners, but I could afford to buy some cheap taffeta and make a ball gown and go to the clubs where those people went, and walk into them like I owned them.

On a Saturday, sometimes even on a Thursday because the stores opened late, I would walk up and down Madison Avenue looking in the windows feeling like, ‘I wish I had on a black wool crepe dress, with high heels, a clutch, big hat and glasses and pearls.’ I would go into a store called Belloccio Uomo. It was owned by one black guy and one blonde guy, they were lovers. I would go into that store and talk to them for hours. We talked about fashion and clothes and what they were going to make me wear. They’d let me try on the clothes and say, ‘You look great in this’ and I’d be like, ‘I can’t afford it.’ But I’d try it all on, get inspired and go and try to copy the shapes.

Even today, when I can afford whatever I want, I very rarely just think, ‘Oh I like that,’ and get it. Spending thousands of dollars on something is not for me. I buy what I need, not what I want. A friend gave me some taffeta recently, and I made a plissé skirt, all by hand. I haven’t worn it yet but I know it’ll look really great over a black suit, worn with a white shirt. I’ve kept it open at the back because I’m going to add pleated tulle that comes out the back. When it’s finished I’ll wear it to a red carpet or black tie event, or maybe a fashion event. I made a sash from the scraps so I can tie the waist and make it a look. Now I want to make velvet embroidered silk grosgrain slippers in the same colour to wear with it.

I went to a charity event with my friend who’s the CEO of Kiehl’s some time ago. They travelled across the country with motorcycles to raise money for Aids. They gave people bandanas and I took all the leftover bandanas and made a kilt from them. It’s got little snaps to keep it on, and it’s pleated. It took me about four hours to make it, while I was watching ‘Le Petit Journal’ on TV. I made flowers from the bandana scraps to fasten to my shirt, and I’ll wear a bandana on my head too. I’ve already got my outfit figured out: I’m going to do a white man’s button-up shirt, low V, wear it low, pop the collar, roll up the sleeves, very casual, tuck it in and that’s it. I’ll wear white tennis shoes or a white lace-up shoe and there you have it. I’ll wear it to a little summer party. It’s been two years since I made it and I haven’t worn it because I’ve only seen my friends at winter events. I cannot wait to wear it so they can die.

A friend of mine made me a gown and I wore it to the Oscars in 2012. A man gown I call it. It was strapless, and I wore it with a man’s tuxedo shirt and a bow tie, over Marc Jacobs velvet tuxedo pants and velvet slippers. It’s funny, people keep asking, ‘Are you trans?’ Or they say, ‘Oh my god, Miss J is an inspiration to trans women all over the world!’ I keep going, ‘But I’m not actually trans,’ but they still think so.

I remember seeing a white man on TV fifteen years ago; he was wearing a skirt and arguing that men should be able to wear one, like, what’s the big deal? I was wearing skirts with full make-up and heels at the same time, but only at night, and I remember thinking, ‘You go!’ Men are still used to their suits and ties. A woman in a suit today is a power woman, but a man in a dress is a cross dresser, trans, a drag queen. Society still tells us pink is for girls, and blue for boys.

This interview was originally published in Vestoj ‘On Masculinities.’

Anja Aronowsky Cronberg is Vestoj’s Editor-in-Chief and Founder.

MR. TOWERS CHANDLER WAS pressing his evening suit in his hall bedroom. One iron was heating on a small gas stove; the other was being pushed vigorously back and forth to make the desirable crease that would be seen later on extending in straight lines from Mr. Chandler’s patent leather shoes to the edge of his low-cut vest. So much of the hero’s toilet may be intrusted to our confidence. The remainder may be guessed by those whom genteel poverty has driven to ignoble expedient. Our next view of him shall be as he descends the steps of his lodging-house immaculately and correctly clothed; calm, assured, handsome – in appearance the typical New York young clubman setting out, slightly bored, to inaugurate the pleasures of the evening.

Chandler’s honorarium was $18 per week. He was employed in the office of an architect. He was twenty-two years old; he considered architecture to be truly an art; and he honestly believed – though he would not have dared to admit it in New York – that the Flatiron Building was inferior in design to the great cathedral in Milan.

Out of each week’s earnings Chandler set aside $1. At the end of each ten weeks with the extra capital thus accumulated, he purchased one gentleman’s evening from the bargain counter of stingy old Father Time. He arrayed himself in the regalia of millionaires and presidents; he took himself to the quarter where life is brightest and showiest, and there dined with taste and luxury. With ten dollars a man may, for a few hours, play the wealthy idler to perfection. The sum is ample for a well-considered meal, a bottle bearing a respectable label, commensurate tips, a smoke, cab fare and the ordinary etceteras.

This one delectable evening culled from each dull seventy was to Chandler a source of renascent bliss. To the society bud comes but one début; it stands alone sweet in her memory when her hair has whitened; but to Chandler each ten weeks brought a joy as keen, as thrilling, as new as the first had been. To sit among bon vivants under palms in the swirl of concealed music, to look upon the habitués of such a paradise and to be looked upon by them – what is a girl’s first dance and short-sleeved tulle compared with this?

Up Broadway Chandler moved with the vespertine dress parade. For this evening he was an exhibit as well as a gazer. For the next sixty-nine evenings he would be dining in cheviot and worsted at dubious table d’hôtes, at whirlwind lunch counters, on sandwiches and beer in his hall-bedroom. He was willing to do that, for he was a true son of the great city of razzle-dazzle, and to him one evening in the limelight made up for many dark ones.

Chandler protracted his walk until the Forties began to intersect the great and glittering primrose way, for the evening was yet young, and when one is of the beau monde only one day in seventy, one loves to protract the pleasure. Eyes bright, sinister, curious, admiring, provocative, alluring were bent upon him, for his garb and air proclaimed him a devotee to the hour of solace and pleasure.

At a certain corner he came to a standstill, proposing to himself the question of turning back toward the showy and fashionable restaurant in which he usually dined on the evenings of his especial luxury. Just then a girl scuddled lightly around the corner, slipped on a patch of icy snow and fell plump upon the sidewalk.

Chandler assisted her to her feet with instant and solicitous courtesy. The girl hobbled to the wall of the building, leaned against it, and thanked him demurely.

‘I think my ankle is strained,’ she said. ‘It twisted when I fell.’

‘Does it pain you much?’ inquired Chandler.

‘Only when I rest my weight upon it. I think I will be able to walk in a minute or two.’

‘If I can be of any further service,’ suggested the young man, ‘I will call a cab, or – ‘

‘Thank you,’ said the girl, softly but heartily. ‘I am sure you need not trouble yourself any further. It was so awkward of me. And my shoe heels are horridly common-sense; I can’t blame them at all.’

Chandler looked at the girl and found her swiftly drawing his interest. She was pretty in a refined way; and her eye was both merry and kind. She was inexpensively clothed in a plain black dress that suggested a sort of uniform such as shop girls wear. Her glossy dark-brown hair showed its coils beneath a cheap hat of black straw whose only ornament was a velvet ribbon and bow. She could have posed as a model for the self-respecting working girl of the best type.

A sudden idea came into the head of the young architect. He would ask this girl to dine with him. Here was the element that his splendid but solitary periodic feasts had lacked. His brief season of elegant luxury would be doubly enjoyable if he could add to it a lady’s society. This girl was a lady, he was sure – her manner and speech settled that. And in spite of her extremely plain attire he felt that he would be pleased to sit at table with her.

These thoughts passed swiftly through his mind, and he decided to ask her. It was a breach of etiquette, of course, but oftentimes wage-earning girls waived formalities in matters of this kind. They were generally shrewd judges of men; and thought better of their own judgment than they did of useless conventions. His ten dollars, discreetly expended, would enable the two to dine very well indeed. The dinner would no doubt be a wonderful experience thrown into the dull routine of the girl’s life; and her lively appreciation of it would add to his own triumph and pleasure.

‘I think,’ he said to her, with frank gravity,’that your foot needs a longer rest than you suppose. Now, I am going to suggest a way in which you can give it that and at the same time do me a favour. I was on my way to dine all by my lonely self when you came tumbling around the corner. You come with me and we’ll have a cozy dinner and a pleasant talk together, and by that time your game ankle will carry you home very nicely, I am sure.’

The girl looked quickly up into Chandler’s clear, pleasant countenance. Her eyes twinkled once very brightly, and then she smiled ingenuously.

‘But we don’t know each other – it wouldn’t be right, would it?’ she said, doubtfully.

‘There is nothing wrong about it,’ said the young man, candidly. ‘I’ll introduce myself – permit me – Mr. Towers Chandler. After our dinner, which I will try to make as pleasant as possible, I will bid you good-evening, or attend you safely to your door, whichever you prefer.’

‘But, dear me!’ said the girl, with a glance at Chandler’s faultless attire. ‘In this old dress and hat!’

‘Never mind that,’ said Chandler, cheerfully. ‘I’m sure you look more charming in them than any one we shall see in the most elaborate dinner toilette.’

‘My ankle does hurt yet,’ admitted the girl, attempting a limping step.’I think I will accept your invitation, Mr. Chandler. You may call me – Miss Marian.’

‘Come then, Miss Marian,’ said the young architect, gaily, but with perfect courtesy; ‘you will not have far to walk. There is a very respectable and good restaurant in the next block. You will have to lean on my arm – so – and walk slowly. It is lonely dining all by one’s self. I’m just a little bit glad that you slipped on the ice.’

When the two were established at a well-appointed table, with a promising waiter hovering in attendance, Chandler began to experience the real joy that his regular outing always brought to him.

The restaurant was not so showy or pretentious as the one further down Broadway, which he always preferred, but it was nearly so. The tables were well filled with prosperous-looking diners, there was a good orchestra, playing softly enough to make conversation a possible pleasure, and the cuisine and service were beyond criticism. His companion, even in her cheap hat and dress, held herself with an air that added distinction to the natural beauty of her face and figure. And it is certain that she looked at Chandler, with his animated but self-possessed manner and his kindling and frank blue eyes, with something not far from admiration in her own charming face.

Then it was that the Madness of Manhattan, the frenzy of Fuss and Feathers, the Bacillus of Brag, the Provincial Plague of Pose seized upon Towers Chandler. He was on Broadway, surrounded by pomp and style, and there were eyes to look at him. On the stage of that comedy he had assumed to play the one-night part of a butterfly of fashion and an idler of means and taste. He was dressed for the part, and all his good angels had not the power to prevent him from acting it.

So he began to prate to Miss Marian of clubs, of teas, of golf and riding and kennels and cotillions and tours abroad and threw out hints of a yacht lying at Larchmont. He could see that she was vastly impressed by this vague talk, so he endorsed his pose by random insinuations concerning great wealth, and mentioned familiarly a few names that are handled reverently by the proletariat. It was Chandler’s short little day, and he was wringing from it the best that could be had, as he saw it. And yet once or twice he saw the pure gold of this girl shine through the mist that his egotism had raised between him and all objects.

‘This way of living that you speak of,’ she said, ‘sounds so futile and purposeless. Haven’t you any work to do in the world that might interest you more?’

‘My dear Miss Marian,’ he exclaimed – ‘work! Think of dressing every day for dinner, of making half a dozen calls in an afternoon – with a policeman at every corner ready to jump into your auto and take you to the station, if you get up any greater speed than a donkey cart’s gait. We do-nothings are the hardest workers in the land.’

The dinner was concluded, the waiter generously fed, and the two walked out to the corner where they had met. Miss Marian walked very well now; her limp was scarcely noticeable.

‘Thank you for a nice time,’ she said, frankly. ‘I must run home now. I liked the dinner very much, Mr. Chandler.’

He shook hands with her, smiling cordially, and said something about a game of bridge at his club. He watched her for a moment, walking rather rapidly eastward, and then he found a cab to drive him slowly homeward.

In his chilly bedroom Chandler laid away his evening clothes for a sixty-nine days’ rest. He went about it thoughtfully.

‘That was a stunning girl,’ he said to himself. ‘She’s all right, too, I’d be sworn, even if she does have to work. Perhaps if I’d told her the truth instead of all that razzle-dazzle we might – but, confound it! I had to play up to my clothes.’

Thus spoke the brave who was born and reared in the wigwams of the tribe of the Manhattans.

The girl, after leaving her entertainer, sped swiftly cross-town until she arrived at a handsome and sedate mansion two squares to the east, facing on that avenue which is the highway of Mammon and the auxiliary gods. Here she entered hurriedly and ascended to a room where a handsome young lady in an elaborate house dress was looking anxiously out the window.

‘Oh, you madcap!’ exclaimed the elder girl, when the other entered. ‘When will you quit frightening us this way? It is two hours since you ran out in that rag of an old dress and Marie’s hat. Mamma has been so alarmed. She sent Louis in the auto to try to find you. You are a bad, thoughtless Puss.’

The elder girl touched a button, and a maid came in a moment.

‘Marie, tell mamma that Miss Marian has returned.’

‘Don’t scold, sister. I only ran down to Mme. Theo’s to tell her to use mauve insertion instead of pink. My costume and Marie’s hat were just what I needed. Every one thought I was a shopgirl, I am sure.’

‘Dinner is over, dear; you stayed so late.’

‘I know. I slipped on the sidewalk and turned my ankle. I could not walk, so I hobbled into a restaurant and sat there until I was better. That is why I was so long.’

The two girls sat in the window seat, looking out at the lights and the stream of hurrying vehicles in the avenue. The younger one cuddled down with her head in her sister’s lap.

‘We will have to marry some day,’ she said dreamily – ‘both of us. We have so much money that we will not be allowed to disappoint the public. Do you want me to tell you the kind of a man I could love, Sis?’

‘Go on, you scatterbrain,’ smiled the other.

‘I could love a man with dark and kind blue eyes, who is gentle and respectful to poor girls, who is handsome and good and does not try to flirt. But I could love him only if he had an ambition, an object, some work to do in the world. I would not care how poor he was if I could help him build his way up. But, sister dear, the kind of man we always meet – the man who lives an idle life between society and his clubs – I could not love a man like that, even if his eyes were blue and he were ever so kind to poor girls whom he met in the street.’

This story was originally published in The Four Million, a collection of short stories by O. Henry, in 1906.

Images courtesy of the Museum of Modern Art (www.moma.org).