'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.
L-R: Satin tuxedo blazer, £240, and trousers, £150, both Jigsaw; Montana pale blue crepe tea dress, £279, LK Bennett; Emilia Wickstead Doreen dress, to rent from £132, Hurr Collective
Rule 2: the shoes
Gone are the days in which you’d have to suffer all day in towering stilettos, although if you are particularly committed to them, I recommend Sharon Stone’s inspired trick of using a numbing spray on your feet. But why bother when there are so many covetable mid-height block heels on the high street? Dressy flats, too. You may be walking or standing a lot, and nothing ruins a fun day out like that ache in the balls of your feet.
Pointed toe slingbacks will be as stylish on race day as they will be for the office or an evening out. A minimalist mule will also be a versatile wardrobe player. Don’t bother trawling the shops for a perfect match for the rest of your outfit. A colour clash actually looks more stylish and exudes far more confidence than a more ‘matchy matchy’ look.
Do keep it smart though; this is not the occasion for your trusty old espadrilles or chunky flat sandals, and if you do invest in a new pair, wear them in at home so they don’t rip your feet to shreds on race day itself.
Top to bottom: Suede ankle tie heels, £110, Boden; Disco Queen platform sandals, £225, Russell & Bromley; Charles & Keith cone heel courts, £55, John Lewis
Rule 3: the hat
Tradition might dictate that you match your hat to your dress, but in 2022, as with footwear, the most stylish racegoers will choose a headpiece that contrasts with their outfit instead.
“I tend to go bold in my dress and see the hat as more of a finishing touch,’” says Telegraph Magazine columnist Virginia Chadwyck Healey. “I also like to kiss people. I prefer a hat or hairband I can greet friends in, so no dipping to bend under a wide brim.”
The summer season is a wonderful opportunity to support British milliners, and you may find that one timeless buy can work with lots of different outfits for years to come. Some favourites include Merve Bayindir, Camilla Rose, Rachel Trevor-Morgan and Jane Taylor.
Padded hairbands and fascinators are also acceptable at most formal events - but bear in mind that Ascot’s Royal Enclosure demands a headpiece with a solid base of 4 inches or more in diameter, so you’ll get most use out of a hat that meets those requirements.
Top to bottom: Emily London Koroleva headpiece, £485, Harvey Nichols; Diane mini pill box hat, £65, John Lewis; Jess Collett Rowan headband, to rent from £36, Hurr Collective
