EM Best Dressed Racegoer Winner: Chester May Festival 2020

Huge thanks for all the GORGEOUS entries for our Best Dressed Racegoer Competition for the Chester May Festival 2020! 

You can see the entries for the Chester May Festival competition here. It was a heated debate amongst the judges but in the end a decision had to be made….so:

The winner of our Chester May Festival competition is the delightfully dazzling Gillian Carpenter in her leopard print dress (see our interview with her below). Highly Commended goes to Sally Harper (B) and Vini Reid. Congratulations!! And thanks to all who took part.

Meet Gill:

Obviously we loved your look for the Best Dressed competition – could you talk us through the outfit?

Firstly, thank you SO much for selecting me, there were so many beautiful outfits!

I spotted the dress on ASOS a while ago and loved the turquoise and lilac shades so when it appeared in the sale I couldn’t resist! The dress was originally a maxi so I took off the lower ruffles until I was happy with the length as I felt it was more race day appropriate. The high neck and the sleeves reminded me of a Japanese kimono hence the fan and lily design of my millinery. I designed and made the hat myself after hand dying all of the components individually.

With so much going on I felt that the accessories needed to be as plain as possible – just as well as I couldn’t go shopping in lockdown!

Is high fashion and dressing up a major part of your everyday life or do you save it for special events?

I’ve always loved dressing up and racing events give me the perfect opportunity to do so! Where else in life can you wear so many different looks combined with millinery and gloves in the same year?!

In everyday life I do love fashion and enjoy following trends but am equally happy to be walking my dog in the rain in my running kit!

When and how do you start planning for any racing outfit? OR What comes first in planning an outfit – the hat or the dress?

The answer to this varies SO much. Sometimes I will source a particular dress and plan an outfit months in advance but I have also discovered a new dress the day before and made my hat at 4 am on raceday! I have to confess I quite enjoy the excitement of a last minute decision!

During busy months such as before Cheltenham and Ascot, I always make my hat at the last minute as my clients come first.

Hat or dress first is an interesting one and I don’t think there should be a set rule. If you see either and love it then just go for it – you will always find a perfect match!

How do you vary your style to keep it fresh?

I love to vary my style. Each race day is a new opportunity  to wear something different and I enjoy taking risks with millinery. I love to try out new techniques and materials which reflect my personality. That’s the fun of racing fashion – anything goes!

What fashion/beauty/racing essentials do you always carry with you for the races and why?

It occurs to me now that there is a theme to this answer , mostly based on bitter  and painful experience! My essentials are: heel grips, foot pads, plasters, painkillers, hair grips, needle and thread, hairspray and lip gloss. My husband’s pockets come in very handy! The weather can play havoc with your look and it’s a long day to spend in your most fabulous shoes.

Do you have any fashion tips on how to keep the cost down whilst still looking fabulous and unique?

If there is one thing that lockdown has taught us it’s that re-styling or re-wearing a previous outfit with a new twist can be really fun and creative. I think that sustainable fashion has to be the way forward and I’m a huge fan of finding a vintage bargain and then working with a local dressmaker to make it my own.

With the right millinery an inexpensive dress can become a  real showstopper (as I hope this entry has proved!).

Of course I love a beautifully made and perfectly fitted designer ensemble but I also believe that looking and feeling fabulous should be available to everyone. At the end of the day, if you love your outfit then that confidence will shine through and there’s nothing more attractive than that!

Which fashion designers and milliners are you inspired by and why?

So many and so varied. I adore the classic styling of the ’40s, ’50s and ’60s, those beautiful, elegant lines of a Dior dress are just my idea of heaven! I work alongside an amazing local designer, Deborah Coates whose work embodies all of those traits.

That said, I also love the flair and creativity that comes with racing fashion. Combining the old with the new, the expensive and the inexpensive, vintage to high street and creating something with your own personal flair is so exciting.

I follow so many milliners and designers and take inspiration from all of them. From Philip Treacy and Stephen Jones to the incredible style and originality in Australia, I love everything from the classic Dior brim to modern sculptural pieces and the sheer fabulousness of feathers and I hope that my style reflects that.

How often do you attend the races and which is your favourite racing event?

I attended racing long before my interest in millinery began so we try to attend as many as possible. Our year always begins with Cheltenham and Aintree followed by a tour of many of the smaller racecourses and usually ending with the [St] Leger at Doncaster. It’s so difficult to say which is my favourite! I love both the winter style of Cheltenham with all the felt and feathers and the fun and variation of Aintree just a few weeks later. I can’t choose between them as I love them for different reasons!

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Do NOT follow this link or you will be banned from the site!

Racing News, What to Wear, Competitions, Features, Betting Tips and More

Join our mailing list to receive the latest news and updates from our team. We'll bring the news to you about once a month. We NEVER share your data.

You have Successfully Subscribed!

Scroll to Top