‘I haven’t dressed up in ages, what do I wear for the races?’

Rediscover your fashion confidence and dip your toe back into something braver. In our Wardrobe Whisperer column, our team will find a solution for every style crisis.

Dear Wardrobe Whisperer, 

I’m going to the Epsom Derby and it’ll be the first time I’ve dressed up in formalwear since the start of the pandemic. I’ve gone down from a 16 to a 14, and want to wear something more modern, but I’m not sure where to begin.

– Louise

Dear Louise,

After two years out of the formalwear fray, I can understand why you might feel daunted by the idea of dressing up again. You may have lost your tolerance for high-heeled shoes. Your go-to dress may no longer be a good fit. And what even are the rules of hats versus fascinators in 2022? Getting it right doesn’t have to be overly complicated though – just consider these three simple rules to guide you back on course.

Rule 1: The clothes

This could be a midi dress, a jumpsuit (a favourite with the Countess of Wessex) or a tailored suit – but don’t buy anything without examining enclosure dress codes carefully. The Epsom Derby is relatively lenient, but for the Royal Enclosure at Royal Ascot, the straps of your outfit must be at least one inch wide, they can’t be made from a sheer fabric, and the hem must fall at or below the knee. This may sound limiting, but it actually filters out some of the less sophisticated looks on the high street.

Some retailers have done the hard work for you with dedicated occasionwear edits – LK Bennett’s is particularly strong, but there are also lovely options at Fenwick and Cefinn. Jigsaw’s hot pink belted tuxedo would be a very chic alternative to a dress.

If you’d rather not attend all your summer events in the same couple of outfits, consider fashion rental: for the price of a high street frock, you could borrow a designer piece by The Vampire’s Wife or Emilia Wickstead from Hurr Collective, which feels like raiding the wardrobe of a very stylish friend. Selfridges and LK Bennett both offer rental too.

Broadly speaking, solid colours are more timeless than prints, although this is a rule worth breaking for a particularly beautiful floral or polka dot – Julia Roberts at the polo in Pretty Woman would be a good muse for the latter. Take a leaf from the royals’ style playbook and choose a skirt with some structure to it, so it won’t fly up in high winds.