How to style a pillbox hat for Royal Ascot

Telegraph

4 hours ago

Suddenly I'm standing taller, as if that imaginary string my mother always harped on about is finally pulling me up from the crown of my head. I'm looking in the mirror at milliner Jess Collett's studio in Notting Hill, London, where she's just placed a petrol-blue pillbox hat on my head, adorned with a navy bow made from her grandmother's old frock.
'This silhouette frames the head so beautifully. When you're talking to someone, the first place they look is your face – a pillbox surrounds the wearer like a halo,' beams Collett, whose whimsical creations have graced many a royal, including the Princess of Wales, Princess Charlotte and Zara Tindall.
Now I understand why the style was such a go-to for timeless fashion icons like Jackie Kennedy and Queen Elizabeth II, who frequently wore the mod, brimless silhouette in a variety of confection-like looks throughout her reign. With this minimalist crown perched on my head, I find myself holding it just a little bit higher.
But the soft-power style is no longer reserved for first ladies and royalty – in fact, if the fashion world has anything to say about it, the pillbox is set to sweep the garden parties and Royal Enclosures of this social season. Forget fiddling with fascinators or awkwardly navigating a big brim à la Inauguration Melania Trump (who may or may not have wielded it to swerve her husband's advances) – a pillbox offers a more modern option for events like Ascot.
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Shop the best pillbox styles
Choose the right shape for your face
How to style your hair and secure the hat
How to wear it at Ascot
Runway to real life
While at Copenhagen Fashion Week earlier this year, I spied pillboxes popping up on stylish Scandis walking down the street, ditto on the runway, where Danish mother-daughter-founded label Herskind sent raised pillboxes down the catwalk paired with luxurious silks and flirty thigh-high boots.
London followed soon after: Emilia Wickstead tapped milliner Laura Cathcart to create sugared-pastille shapes in shades of pistachio and café au lait, complementing a very 1960s collection inspired by Tippi Hedren's style in the Hitchcock horror, The Birds.
Even British Fashion Council NewGen award winner Tolu Coker, applauded for her distinctive brand of cool mixing Nigerian influences with classic tailoring, paired an asymmetrical white pillbox by Virna Pasquinelli with a puffed-sleeve minidress in her Autumn 2025 collection, giving the look a modern feminine feel.
Collett confirms the versatility credentials of the pillbox: 'You don't really feel like you've got it on; it's not intrusive in any way. Especially if you're a queen, or at an event where you'll be kissing people, your face needs to be visible. You don't feel the pillbox when you're wearing it. It's a good everyday piece.'
Isabella Rose Davey, formerly of the British Fashion Council and now chief operating officer of Copenhagen Fashion Week, makes the case for the everyday wear. She recently inherited a pillbox style from her mother, who used to work in Uzbekistan: 'On one of her trips she purchased a beautiful Astrakan hat – it is such a special piece, both in memory and in design.'
Though Davey says her dream outfit to pair the traditional headpiece with would be 'a smart long coat from the likes of Herskind and a princess dress by Nicklas Skovgaard underneath, with stilettos by Icelandic designer Kalda,' when she sends me a photo of herself wearing the heirloom, it looks just as chic paired with a jumper and jeans.
It's not too far of a stretch to imagine the colourful straw styles I wear here elevating a tailored look for a smart summer lunch, or even a pop to the shops (why not? Looking stylish at Waitrose never hurt anybody…). The clean lines of a pillbox means it plays well when dressed both up and down – but if you're not entirely convinced, I recommend renting the style for low-stakes experimenting.
Many milliners, including Collett, offer rental services directly through their websites, and platforms like By Rotation also offer a wide selection.
Whether you plan to don a pillbox at a champagne-and-horses formal event or dare to wear one in your everyday life, one thing is clear: with classic styles come classic inspirations. Women of all ages and sartorial orientations are catching on to the confidence-boosting effects of a pillbox, and the return of this retro silhouette sees the late Queen's legacy resonate with a whole new generation of stylish women.
Pick your pillbox
How to wear the pillbox to suit your face shape
The good news: according to Collett, it's an easy hat that suits most people. Though there is no wrong way to wear the pillbox per se, she stipulates that there are some rules to styling it for your specific face shape. If you have a longer face, avoid placing the hat too far back on your head – this will elongate your face in an unflattering way.
Opt for an angle that sits closer to your forehead, or even cuts across it, similar to how I've styled the toffee-coloured pillbox from Jane Taylor, who counts Beyoncé and the Duchess of Edinburgh as clients. This also works for those with rounder faces – placing it at a jaunty little angle will give you some sharpness. The Pan Am flight attendant-ness of it all just adds to the fun.
And if you've got an oval face, lucky you: most angles (and hat styles in general for that matter) will suit you. A pillbox is also great for those on the petite side, as it adds height and draws up your frame rather than drowning you in a big brim.
How to style your hair and secure the hat
Sam McKnight, the legendary hairstylist responsible for Diana's sleek 1990s makeover, knows a thing or two about hair that's both regal and contemporary.
'When accessories are formal, I love to balance that with a more modern, undone look,' he says. 'Effortless waves and texture feels like you haven't tried too hard and keep things looking fresh and youthful.' He advises against hairstyles with too much volume and height, since you're already getting that from the hat itself.
Collett, meanwhile, is a fan of a low bun with a pillbox – or even this season's most talked-about haircut, the edgy bob (Jackie O looked sharp in the silhouette for a reason).
Now for ensuring your chapeau doesn't blow away in the summer breeze: most pillboxes come with a comb inside to secure the hat to your hair. For added grip, Collett adds an elastic to her hats, which is meant to be placed at the back of the head, underneath the hair. In her studio, she shows me how to use grips to pull out pieces of my hair to camouflage the elastic – and even takes a sharpie to it, the same shade of brunette as my bob, to further hide it:
If you're after a Fort Knox level of security, opt for a hat pin on top of it all. Simply stick it through the back of the hat, ensuring it grabs onto your hair, and pull it out the other side.
How to wear it at Ascot
When it comes to styling the pillbox for formal events like Royal Ascot, Collett says it's all about the trimmings: a simple style calls for clean tailoring. Think Jackie O's pastel suits and matching hats – or even Demi Moore, who wore a veiled, gothic pillbox paired with black trousers and a tailored t-shirt on a red carpet last year.
I echo this approach in my matching Me+Em bouclé skirt and top, allowing the hats to take centre stage.
For a design with a bit more zhuzh, such as the cherry-red Jess Collett floral piece or the black-and-white button style from John Lewis I'm pictured in above, a floatier dress would match the energy nicely.
Think Queen Elizabeth's joyful bubblegum pink pillbox – complete with 25 pink 'bells' hanging off the back to commemorate her Silver Jubilee – which she paired with a breezy pleated coat dress.
Shoot styled by Sophie Tobin