Spring 2022

Not Just a Day at the Races

by Jenny Roberts

I have been lucky enough to have been involved, for over 11 years, with a number of racecourses in Yorkshire; judging competitions during the busiest event: ‘Ladies’ Day.’

For those of you new to the world of ‘Best Dressed’, a little background… The majority of the racecourses across the country, but also some overseas, hold ​an annual ‘Ladies’ Day.’ Guests are encouraged to dress-up in all their fineries including hats! On these days, a ‘best dressed’ competition is usually exclusively held for women, but more recently there have been competitions for men and even children’s prizes too! These events are always really exciting and quite a difficult job for the judges, as those who enter go to extraordinary lengths to put on a good show!

I have been lucky enough to be the chosen judge for both Thirsk Racecourse and Ripon Racecourse in North Yorkshire and have seen the competition both grow in number of entries, prizes and kudos.


How does the entry work?

These events can vary from racecourse to racecourse. Some of the large courses, like York, deploy a catwalk where entries are able to ‘strut their stuff’ down the runway each day. The events can run over five days, with contestants battling it out for the overall ‘best dressed’ which is decided on the final day of the festival.

During some events, it’s not unusual to find judges roaming around the racecourse, armed with a finite number of invitations, which they selectively issue to those ladies who are then invited to participate in the competition.

Some racecourses encourage all the ladies, who want to enter the competitions, to join a line-up, often in the parade ring, where the judges swiftly make their selections. This can often be a frenzy of entrants and invites, as the preliminary selections must be carried out between races! Usually, the preliminaries are whittled down to a final of 10 entrants, who battle it out for the final prizes!

Sometimes the actual ‘Ladies’ Day’ is a sponsored event, which can demand certain etiquette from entrants. For example, the Qatar Goodwood Festival is a particularly special event. It has high expectations regarding the dress code. I have designed and created many hats for ladies attending and noteworthy is the expectation to dress in colours of pale blue and white, especially for the competition, which represents the branding of the sponsor.

What are the prizes?

Often a prize will be given for the ‘Best Hat’, usually with some runners up. It is also usual for a ‘Best Dressed Lady’ to be awarded, with runners up too. However, this can vary depending on the racecourse.

While expectations of entries can be very high, they only serve to reflect the fabulous prizes on offer, especially when the event has a major sponsor. I have seen winning entries walking away with prizes such as: spa breaks, trips to Dubai to the ‘World Cup’ racing events, a bespoke hat, vouchers for high-end clothes boutiques, mini-breaks in 5-star hotels, money to be donated to a charity of choice, tickets for future races and even a Mini Cooper car!


How does the judging work?

I am often asked how I make my choice when judging competitions. Firstly, I always ensure that every woman is made to feel like their efforts have been appreciated; taking as much time as I can to carefully walking up and down the line, engaging with the entrants, looking at their outfits and millinery. As I have become more experienced at this very observational-demanding role, I have been able to spot fabulous millinery and style straight away. Attention to detail is key!

I take great care to thank all the ladies who have bravely put themselves forward; making an incredible effort, which needs to be acknowledged. Usually, I am then able to issue 10 ‘finalist’ cards. Those ladies not selected to be finalists, are then thanked by the Presenter and they then leave the Parade Ring, while the finalists remain for the final selection!

From the 10 finalists, a winner and 2 runners-up are selected for ‘best hat’ and the same for ‘best dressed’. It has been known for a lady to win both categories, although I do like it most when there is a broader range of winners.


How are the winners chosen?

I am often asked what makes a winning outfit or millinery, and my answer is always the same. It isn’t that one style is more superior to another, it is often more down to the taste of the judge. For me personally, especially when it comes to millinery, ‘bigger’ hats are not always better! I look for the originality of the design and the complexity and quality of technique in the millinery. I can spot hand-finishing at a distance, which comes from years of creating millinery myself. I also look for how suitable in style and design the hat is to the wearer, it’s just that ‘je ne sais quoi’ that makes all the difference and the lady, of course, sparkles!

For ‘Best Dressed’ I consider the whole look, which includes: accessories, millinery and outfit; questioning...how harmonious the whole ensemble is, how well it complements the wearer, how effectively it reflects the seasons or weather. I make my final decisions based on how well the ‘look’ has been compiled; dressing with flair is always noticeable, and always trumps those outfits which have been put together just because the individual pieces match.

What I don’t look for is the most beautiful women, the winner is not necessarily the youngest or slimmest lady; it genuinely is how well the overall look is presented. It is sometimes very heart-warming when a more mature lady wins, who often seems the most surprised to come out on top. For me style is when a women knows herself, she dresses to reflect her true self and this radiates in her confidence.

The outcome from judging these events can sometimes be very interesting. I always take great joy when I uncover that I have chosen an aspiring milliner who has created their own look and hat. One of my favourite winners of ‘best hat’ was a lovely lady called Daphne. She presented herself in the most beautiful vintage hat, which I later discovered was from a vast collection of vintage hats she had collected over 40 years. I was very fortunate to be invited, by Daphne, to view her amazing collection; discovering how accurately she used thread and materials, from the same period as the hats, to lovingly restore each piece she had sourced from around the world!



How does sponsoring the competition work?

As a sponsor, I provide the prizes for the ‘Best Hat’ competition. This is often a bespoke made hat for the winner or a hat-hire. In more recent years, I also provide a prize of a masterclass in millinery, which is very well received. The nature of the prizes I award, often result in forging a continued relationship with the winner of the competition and it is always lovely to see them again at the races.

At Thirsk Races, as a sponsor, I am highly privileged to have a race actually named after me. This is really special; my name appearing on the race-card and all over the country on the Fact Listing. It’s a real ‘buzz’ to see ‘The Jenny Roberts Handicap’ on the screen. This race however, comes with some extra responsibilities, which I take very seriously.

I first have to view the horses in the parade ring, before the race and choose the ‘Best turned-out Horse’. This, I must add, is more than just my favourite colour in the jockey’s silks and the prettiest plaited horse’s mane! I always consider how many hours the grooms have spent preparing the horses for the race; keenly scrutinising the horses for how glossy their shiny coats are. Attention to detail also being given to how immaculate their hooves are presented too. In addition, I look for a well-turned-out groom or handler, which can really finish the overall ‘look’. It’s also considered ‘good luck’ for the horse in the race, to have been chosen for ‘best turned out’. Clearly it must be, as the winning groom is always very happy to be awarded with the cash prize for their efforts!

Following the judging, I am given the great pleasure of presenting the prize to the winning owner, in the winner’s enclosure; its lovely to find out more about the winning horse and reflect on the race with them; celebrating their achievement.


To conclude…

All in all, I love being involved in Ladies’ Days, not just for the fashion, fun and festivities, but also for the relationships I have nurtured over the years; friends I have made at the racecourse. I am so privileged to be part of these special events, where I love meeting many lovely ladies who are brave enough to put themselves ‘out there;’ wearing their style and fineries with such pride and elegance. It’s wonderful to be part of long-standing traditions that make ‘a day at the races’ a truly memorable event. After-all who doesn’t love dressing up, looking and feeling fabulous while watching a jolly good bit of racing!


Jenny Roberts