There are few events on the British social calendar as sartorially charged as Royal Ascot, where fashion isn’t just a statement, but a spectacle.
“Royal Ascot is one of those rare moments where high drama is not only allowed – it’s encouraged,” says celebrity stylist Deborah Sheridan-Taylor.
“But […] individual flamboyance is fabulous – on one person. Multiply it across a crowd, and suddenly it’s less couture and more costume department.”
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With Royal Enclosure headwear rules as stringent as they are traditional, knowing how to channel flair whilst adhering to formality is key.
As Sheridan-Taylor says, “Keep proportions elegant, structure strong and try not to let your hat enter the enclosure five minutes before you do.”
Know yourself before picking a headpiece
Pulling off a headpiece begins long before popping anything on your head. “It sounds obvious, but the real trick to pulling off a headpiece is knowing your personal style first,” says Sheridan-Taylor.
“What do you want to say? Which era or decade do you want to lean toward? You don’t want to feel like you’re auditioning for a role in My Fair Lady.”
Instead, opt for silhouettes and colours that suit your everyday style. “The fascinator should complement your outfit, not dictate it,” she says.
That said, Ascot remains a good playground for experimentation. “But if there’s ever a time to play, it’s now. Just make sure you still recognise yourself in the mirror and won’t cringe at the photos the next day!”
If you’re unsure where to start, Sheridan-Taylor suggests creating a Pinterest board or images of hats and outfits you’re drawn to.
“Even better if you’ve been to Ascot before, as you can refer to real-world looks you loved,” she explains. “The best-dressed women aren’t necessarily the flashiest – they’re the ones who look completely at ease in what they’ve chosen.”
Build your look around one hero piece
If you’re staring at a riotously floral dress wondering how to style it, Sheridan-Taylor says it’s important to stay restrained.
“Pick your battles,” she says, “choose one clear element and build around it. If your dress features a bold print – say, multicoloured irises – just pick out one of the colours and echo it in your accessories.”
If that proves too fiddly, then Sheridan-Taylor says to ignore the print altogether and match your hat to your shoes instead. “That top-and-bottom pairing works wonders, magically pulling the whole look together.”
And one accessory that may have slipped your mind is make-up.
“Don’t underestimate the power of good make-up,” she says. “Don’t leave it as an afterthought – a well-made-up face is just as important as the hat that sits above it.
“The right smokey eye or plum-coloured lipstick can make the whole look sing.”
Stylist-approved millineries
When it comes to her favourite millinery picks of the season, Sheridan-Taylor has some British-based labels she loves.
“I will always love the Zellova pillbox from Emily London. It’s simple and suits most faces, always understanding and delivering the assignment.”
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For those after a slightly higher-drama showstopper, she recommends feathers, “[it’s] super theatrical, and worn with modern tailoring like a sharp white trouser suit is just perfection.”
And for a retro take on the traditional headpiece, the Sixties are having a resurgence in formalwear, and Sherdian-Taylor says pillboxes are the way to go this season.
“I’m obsessed with the Silk Petal Bomb – clue’s in the name – by Rachel Trevor-Morgan,” she says.
“It’s playful but sculptural, the kind of piece that turns heads without even trying. Worn with a knee-length shift dress and a sharp cat-eye flick, it sits somewhere between Julianne Moore in A Single Man and peak Jackie O.”
Phase Eight Mini Bow Boater Fascinator, £49 (was £69)
Whiteley Melody Upturn Feather Trim Fascinator, £215, John Lewis
John Lewis Arabella Polka Dot Fascinator, Blue, £69
Be brave – but don’t overdo it
Whatever you wear to the races, don’t dilute your personality in the pursuit of etiquette.
“I’m always in favour of originality – that means stepping away from polite colours in traditional shapes unless they’re genuinely you,” says Sheridan-Taylor.
“Too often, people either throw everything and the kitchen sink at a look, or retreat into timid, apologetic outfits. Neither works,” she says, “be brave and as they say, mighty forces will come to your aid.”
This is Royal Ascot after all – one of the few occasions where extravagance and formality walk side by side. Just make sure your fascinator doesn’t get there before you do.
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