After six Pimms, 20 squandered pounds, two purchased hats, and one final race at Royal Ascot, the five-day premier horse racing event in England, Rachel and I board the crowded train back to London and end up sitting in the First Class car. We’d somehow found ourselves, two Americans, returning from a day at the races.

A slim woman in her thirties with long, blond hair enters our small coach. “Just ladies in here, is it?” she asks in an English accent, smiling and glancing at us. “This is the smallest First Class coach I have ever seen.” She adjusts her black-and-white checked dress and slips her shoes off as she sits down at the table next to us.

“Did you win any today?” I ask her.

“I won on every race,” she says, smoothing her blond hair into a long ponytail. “It was a winning streak.” She looks around and points to the narrow aisle between our seats.

“Is there going to be a drinks cart on this train?” she asks. “How could it even fit in here?”

She places her black hat on the seat next to her and we start to make small talk about the strict fashion rules at Royal Ascot this year. “Oh, I just thought the Royal Enclosure this year was appalling. Just appalling. Some girls slipped in wearing mini-skirts, as if it’s a nightclub. I have nice legs, too, but this is Ascot. A rule is a rule,” she says. “Dresses should hit the knee and hats need to have a base of four inches or more.” She gestures emphatically: “Those are the rules. That’s what makes it so English. That’s what makes it Ascot.”

“My mother won’t even come to Royal Ascot anymore,” she adds.

 •••

Most girls grow out of the crazy horse phase as soon as they discover boys, but my friend Rachel—who is 28 years old—was intent on getting me to attend Royal Ascot with her this year. I agreed, even though I knew little about it: I assumed it was an English horse race and that we’d get to drink gin outside. It was only after an elaborate effort to secure tickets (or badges) to the restricted Royal Enclosure section—a process that, for Americans, involves writing to the US ambassador to the UK and sending in character references by mail—that I began to wonder what I had gotten myself into. Suddenly it began to feel less like we were going to a horse race and more like we were going to Prince Charming’s ball.

The five-day horseracing event dates back to 1711. Members of the Royal Family are always in attendance. The dress code is strict, and it’s only gotten stricter, as a way to stave off unsuitably dressed attendees. Inside the Royal Enclosure, which Rachel and I would have access to, women’s dresses must be knee-length, straps must be at least an inch wide (nothing strapless, no halters, no bare midriffs), and hats are required for both women (FOUR-inch base minimum) and men (top hats like Mr. Peanut). In case that wasn’t clear enough, Ascot put out this mesmerizing video for guidance.

In contrast, the Kentucky Derbymerely states that tennis shoes, jeans, shorts or athletic apparel are not allowed. Hats for ladies are recommended, and men can wear khakis. Next to Ascot, the Derby looks like a picnic at a high school softball game.

I’ve never witnessed this world before, and for good reason: it’s really hard to get inside of it. My English husband is aghast that I am allowed here because even hecan’t gain entrance into the Royal Enclosure area: all English guests must be sponsored by an existing member who has attended the annual event at least four times. Even babies and young children aren’t allowed here (minors aged 10-16 are admitted on Friday and Saturday only).

Even though I moved to London last year, I hadn’t brushed against the posh English sphere in the slightest. I often ride the red double-decker buses on bridges across the Thames while gazing upon Big Ben, but even Big Ben can’t shut out the fact that the man sitting next to me is blowing his nose directly into his hand. Watching Downton Abbey is far closer to experiencing high society England than living in London. When Rachel asked me to accompany her to Royal Ascot, I decided that I wanted to experience that world up close, just this once. What was it really like?

The week before, we went shopping for our requisite hats. We were hopeful: the hats were so flowery, so whimsical, and so perfectly unflattering. Every hat in the store seemed to transform us into either the Mad Hatter or the Dowager Countess Grantham.

The only beautiful, flattering ones were incomprehensibly expensive. With our money pooled together, Rachel and I could afford one relatively nice hat between us. We debated whether getting into Royal Ascot was akin to getting by a bouncer at a bar when we were under 21 with only one fake ID between us. Could Rachel wear the hat and, once safely inside, send someone else to pass it back to me?

No, says a woman in the department store, firmly. Hats must remain on at all times. “I know women who have been turned away at the Royal Enclosure,” she informs us. Who would actually turn women away? The fashion police, obviously. Officially known as Dress Code Assistants, they wear shiny silver dresses and rule with an iron fist—if your hat isn’t suitable, they will give you another or offer to sell you one. If your dress has spaghetti straps, they will forcibly drape pashminas over your shoulders.

I settled for the cheapest hat I could find (it looked like a frilly white Stetson with gauze and a bow) and Rachel caved and purchased a fancier, angled navy hat that dipped towards her shoulder.

A few days later, we took an hour-long train to Ascot, a town 25 miles west of London. We walked in a crowded procession—a sauntering sea of colorful hats—until we reached the entrance to the grounds. The fashion police were guarding the entrance. One policewoman tapped a lady on the shoulder who was holding her hat in her hand. “Madam,” she said, and pointed to her head. “Your hat.” Another measured the base of woman’s fascinator (one of those headbandy-feathery things that make women look like birds) to ensure that it was at least four inches in diameter (a size that would render it, I kid you not, a “hatinator”). Men and women who arrive unprepared were offered outfit fixes for purchase. The assistants were half fashion police, half that mean saleslady in Pretty Woman.

I wore my Royal Enclosure badge and slipped on my hat. I felt a little like Indiana Jones, infiltrating a secret society. We both passed muster and made our way into the manicured grounds that surround the stadium and then to the tearooms, where Rachel informed two men that we have a reservation for 1 p.m. They looked back at her, puzzled. Men in morning dress, it turns out, look an awful lot like waiters.

We wander around until 2 p.m., when everyone gathers around the racecourse fence and waits for Queen Elizabeth II &Co to go around the track in horse-drawn carriages. The band was playing an instrumental version of Adele’s “Skyfall.” Earlier, the posh crowd had been buzzing away in their own conversations, but when the Queen finally rounds the corner near the finish line, the men remove their top hats, and a hush falls over the grounds.

In her horse-drawn carriage, the Queen, Prince Charles and Camilla glide by. The horsemen are in their traditional red uniforms, the horses are white and the Queen, in a light pink suit and hat, look so regal, but her expression seems blasé. This is, after all, her 60th year on the throne, and each day at Royal Ascot opens this way, so she’s easily done this routine some 300 times. Princesses Beatrice and Eugenie follow in their own carriage, and pass by so close we can see them scowl.

It feels like a still from a movie that would be played on A&E: the band members wear those furry black hats (bearskins), they begin to play “God Saves the Queen” and horse-drawn carriages trot past while men in top hats and women in fascinators hold their breath. They pass, and it’s over. The man next to me puts his top hat back on and begins to talk about his summerhouse. At Ascot, everyone is on perfect behavior. No one breaks character. To better fit in, we must drink the Kool-Aid. And here, the Kool-Aid is Pimms.

On the lawn, a few Pimms in, every conversation I hear is scripted like a parody. “Oh look at you, you’re matching! Even your toes and fingers match!” a man tells a woman dressed in fuchsia from top to bottom.

“Oh, yes!” she says. “I had my nail varnish out last night, but you know how when you paint your nails you can’t do anything! I just had to lay on the bed like this!” She slinks into the posture of a horizontal zombie while still managing to stay on her feet.

“Did you really? Well, that’s very sexy!” the man says to the woman and her husband. “Did he jump on you? ‘Mind the fingers!’”

“Oh, it’s the day-glo orange woman again.”

“Such an unfortunate color.”

“Remember two years ago when it was so terribly hot and we all wore bowlers hats?”

“And Guildford station was full of men in bowler hats! I had to get the later train.”

A woman jumps in: “I used to ride horses wearing a bowler hat.”

“You didn’t!”

“I did!”

And then:

“I made such a lovely duck dinner last night.”

“Oh, we men are so good, so versatile, aren’t we? What did you serve with the duck?”

“Oh, broccoli, pasta, garlic bread. We bought the duck and wrung the neck.”

“Oh, terrible! Did you feel terrible?”

“They only live eight weeks!”

“Do they?”

“Well, it’s easier to pluck their feathers when they’re young.”

“Is it, really? Well, I imagine it does damage the skin if you wait until they get older.”

“And it’s such a good meal because you can have either red or white wine with duck.”

We lose about £20 (or $31) on the first race, so Rachel and I give up and leave the lawn to wander into the Royal Enclosure garden. We pass Rosé Bar, where everything—the champagne, the wine, the cupcakes, and the macaroons—is pink. We also pass a restaurant serving lobster, crab and caviar. Last year, 4,500 pounds of fresh lobster, 35,000 asparagus spears and 30,000 chocolate éclairswere consumed during the week.

Within the Royal Enclosure, there are more layers of exclusivity. In the garden, gentlemen’s clubs, private members’ clubs, and The Jockey Club are members’ only areas. We are not allowed inside, but can gaze upon the people eating at tables with white tablecloths. Nevertheless, I do manage to sneak in long enough to get a snapshot of the wall of patrons’ top hats in the Royal Ascot Racing Club.

Even though I keep waiting for someone to call us out for being impostors, everyone we encounter or accidentally bump hats with is very polite, which is at once a relief and a disappointment. In London, I’d never come across such a concentration of these Horray-Henry types and the constant refrain of “Oh my dear old chap, that was delightful,” begins to rub off on us in a bad way. Whenever either of us accidentally lets ourselves slip into an English lilt or use English jargon, the other one quickly threatens to slap her in the face. We must make sure we don’t become actual impostors.

During the half-hour intervals between races, we mingle and leave the Royal Enclosure to wander around the Grandstand Admission section. This area is more egalitarian and less expensive to attend and has a marginally more lax dress code. It still feels fancy, but is slightly more crowded and has more casual dining options (fish and chips and sandwiches are available). I spot one drunk woman who has removed her shoes and keeps asking her friends where they are going to go out to later. Her accent doesn’t match the posh ones around us, but I’m too much of an outsider myself to place it. Here, we can afford the food. All the better, because even though by the end of the day I’ll have won on a horse named Dawn Approach, I still have a net loss of £20 (or $30). We down two more drinks, wait out the final race, and then head to the train.

•••The blond woman crosses her legs. “Five years ago, Royal Ascot was the crème de la crème. Then, it became appalling with girls wearing fascinators instead of hats in the Royal Enclosure. Strapless dresses. Finally they tightened the rules. Even so, this year, I saw someone in six-inch sparkly stilettos,” she says, shaking her head. “This is a daytime horse race, not a nightclub.”

Rachel and I nod in agreement, as if the sparkly stilettos also offended us and violated our own personal code of fashion protocol at this, the first horserace either of us has ever attended.

Her phone rings. What followed was a conversation that resembles the over-the-top pretend conversations my husband and I have when we put on fake posh accents.

“Darling,” she says into her phone. “Mary is going to give my shoes to the Captain, and he’s going to drop them off at my London flat. And I told the Major that he could take a bottle of champagne as a thank you, so you take one bottle and give the other to him.” She laughs. “Thank you again, Darling,” she says and hangs up.

She turns to me. “What’s the fastest way to get from the train station to St. Paul’s?” she asks.

“There’s a bus that takes you directly there,” I tell her and she says, “Oh no, I don’t do buses. Taxi or the tube.”

“A taxi might be expensive,” Rachel says and the woman replies and shakes her head, “Oh, I don’t care about the money.”

Rachel and I finally cast aside our hats and begin to relax as the train approaches London. Playing posh English was fun for a day, but we were happy to return to a reality where we could bear our shoulders and speak improperly and not pay through the nose for a cup of tea. The woman from the train, like the other attendees inside the Royal Enclosure, seem to be trying to hang onto a society that only exists in these brief moments that they have to construct themselves. The world has slowly moved away from such elitism in daily life, even though it still has a long way to go.

Still, the next day when I’m on the bus and the girl in front of me begins flossing her teeth, I find it almost reassuring to know Royal Ascot week will always be one moment of Old England frozen in time, where everyone is impeccably groomed and gracious as they wave to the Royals and sip their cocktails. They have one perfect week to live out their posh, privileged glory—and we have plenty of occasions for the nightclub.

Previously published in The Hairpin.

GRADUATES IN WONDERLAND is out now.
All photos by Jessica Pan