‘There are moments of formal dressing where one is humbled by the rules of it all’: A New Yorker tackles Royal Ascot for the first time

In the mind of an American, there is a gamut of undeniably British traditions. There is Wimbledon, afternoon tea, and a pint at the pub. Royal Ascot, the yearly horse races that take place at the eponymous racecourse just outside of London, is certainly a part of that gamut too. It takes place over five days and is not so much a horse race as it is a day of merrymaking — with a side of horses whizzing by in the background.

The Royal Procession at Royal Ascot 2025: Day Three - YouTube

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During her reign, Queen Elizabeth II was known to attend all five days — given her obsession with all things equine. These days, attendees are treated to a rotating case of characters from the Royal Family and their friends who appear during the royal procession. This occurs every race day at 2pm sharp when a troupe of horse-drawn carriages make their way down the straight of the race track to thunderous applause in the blazing sun.

While watching the royal procession I was struck by how many Americans clamoured and craned their necks to get a glimpse of the royal family, myself included. Meanwhile, many of the Brits, despite the applause, looked nonplussed — as if a family member or longtime friend had just sauntered in. Unless you count the American presidency, a power position we must spar with every four years, we Americans have nothing like this; a person or family who is, although maybe sometimes a bit divisive at the dinner table, a member of the family nonetheless.

Each of the five days — Tuesday through Saturday — has its own personality. Tuesday is referred to as ‘member day’ and mostly reserved for members of racing clubs and their guests. Wednesday brings the Princes of Wales Stakes, a high payout race, making it the best day for racing aficionados. Thursday is referred to as ‘Ladies Day’, and famous for its bold fashion. Friday is the most social, and Saturday, the last hurrah — an all out bash. I attended over two consecutive days. On Thursday, I joined Silent Pool Gin, the official gin sponsor of the races, and on Friday with British bespoke leather goods maker, George Cleverley. (Reader, full disclosure: I have a product collaboration with the company.)

Brands like these, as well as families and equestrian groups including owners, trainers, and families of the jockeys, play host in the Royal Enclosure, the upper sections of the hulking stadium of seating. The Royal Family is known to make their rounds, visiting these guests to compare notes on their favourite horses, including The Princess Royal (above in blue), in the next door box, binoculars in hand.

The George Cleverley suite also boasted an appearance from two Michelin-starred Chef Alex Dilling, who produced the afternoon’s pre-race luncheon.

The Royal Enclosure has a strictly enforced dresscode. Women must wear a dress or skirt that falls ever-so-slightly above the knee, or lower, and ‘a headpiece or hatinator with a minimum base diameter of 4 inches'. Men are expected to wear morning dress and a top hat, worn only when outside in the common areas or when viewing the races from the outdoor seats. Any disputes are taken to the ‘Dress Code enquiries’ office where we joked that you might be given a thumbs up or down by a fearsome old granny. Instead, there are plenty of options on-site to fix an ensemble — for a price of course.

I was told by an ornery guard that one’s name badge and hangtag must always be visible. Both come with your name handwritten, and the colours change each day to avoid copycats. Women usually place theirs on their handbag; some men insist it should be worn on the left lapel so that it’s easily visible when shaking someone’s hand, but I saw a mix of both left and right…

I don’t consider myself a layman when it comes to style, but there are moments of formal dressing where one is humbled by the rules of it all, which are so steeped in tradition that there’s no bucking them. I remember my first time attending a ball in Vienna a few years ago, and wrestling with ‘frack’, the shorthand term for white tie, which requires an exact layering of collarless shirt, rigid collar, piqué vest and bowtie all in stark white and pinned at the back of the shirt, and topped with a black tailcoat. Morning dress for the Ascot Races felt in many ways the same.

Morning dress may be de rigueur for weddings in the UK, but it's nearly impossible to find in the US, and if you do find it, it’s likely only available as a custom order with a six-month lead time and a five-figure price tag. Time was of the essence though, and I saved the hunt for my own morning dress when I arrived in London. Whilst staying at The Stafford, just a short walk away from the menswear Mecca of Jermyn Street, I decided to visit New & Lingwood, which offers a range of options that go against the grain of tradition, just enough. There I sourced my trousers, waistcoats, ties, tailcoat, and socks. Yes, black socks are absolutely required.

I later found two vintage top hats at Hornets, the charming Kensington vintage shop. Why two top hats? Well, the thought of repeating a top hat two days in a row felt ghastly, but as it turns out, my charming vintage grey top hat was the most ghastly thing of all, as I was told by a seasoned Ascot veteran (who shall remain nameless). Also in the ghastly department were the ‘oh-so-American’ buttons on the collar of my new Oxford shirts.

I suppose I’ll need to save them for next year’s Kentucky Derby instead!

My black silk top hat was much better received, and I found there to be an unspoken measuring contest in the height of the top hat, with the tallest commanding the highest prices. Go figure.

Though Americans may affectionately refer to it as ‘tailgating’, the pre- and post-race celebrations in the car parks — or parking lots as Americanos would say — are unlike any I’ve ever seen. The cars themselves are such rare specimens that it’s a wonder we’re allowed near them, and a favorite of mine included a vintage red Land Rover that had been modified to limousine length. Spilling out the back of each of them is usually an exceptional picnic, complete with full sets of porcelain plates, tea service, and candelabras. Champagne is obviously in no short supply, usually Bollinger.

The energy across the board was overall convivial; cars shared snack supplies, offered to loan corkscrews, and played music from their sound systems. The only thing left missing may have been a hot dog, hamburger, or perhaps some Cheez Whiz…

The most fanatically-organised tailgates unfolded in ‘Car Park 1’, the spots closest to the entrance of the racetrack, located just a stone’s throw away from the tents set up by London members clubs such as The Garrick and White’s. The scene at these tents was strikingly different, with the seating facing outward, almost akin to a Parisian café, creating a sort of tense runway or school cafeteria (depending on what you’re wearing) where any passerby might feel judged by the seated crowd.

In the same section, there was a handsome display of hot air balloon-inspired dining tables arranged by Beaverbrook hotel. Many an Instagram couple took their turns dining here.

As the crow flies, the racetrack is 30 miles away from central London, but traffic can be arduous. I was spoiled on Friday with a helicopter ride from London’s Battersea heliport with George Cleverley’s CEO and owner, George Glasgow Jr. More interesting though is the return to London following the races, from a makeshift heliport, set up in a field close to Car Park 1.

Though, aside from the helicopters, there was very little indication that you were in a heliport. There was a full bar, air conditioning, and plush seating for the women (and men) to perch on and kick off their shoes — which many of them did, heading towards their transport with heels in hand.

I quickly realised that people-watching is half the fun at Ascot. While the horses race on the track, the guests showpony themselves off it, peacocking around the Royal Enclosure. In the following pictures, you’ll find a few guests who stood out to me while I made my rounds — plenty of them turned heads wherever they went.

In all, a day at Ascot has drifted far, far away from its origins as a day purely for horse racing (or was it ever just that?). It is certainly an exercise in unabashed excess, but if you can bury your head in the sand from the wider world and accept that it’s all just one big celebration, then you’re in for an unforgettable time. I’ll be there next year, with a bottle of Bollinger in one hand and my top hat (black) in the other.

Did I miss anything? Send me your Royal Ascot recommendations and feedback via Instagram.