While we wait for June and its glamorous horse racing season to arrive at the Royal Ascot, the anticipation of who’ll wear what has got us thinking back to the 1980s and 90s, when the late Princess Diana caused a fashionable ruckus in bold, inventive headgear.
In 2026, however, it is out with the bold excess of the eighties and in with the romantic modernity of the 1920s, if Diana’s beloved hat designer has anything to do with it.
Three months out from the opening of one of the UK’s most anticipated sporting events, Stephen Jones announced he was launching new pieces as part of Royal Ascot’s millinery collective.
For his contribution, the 68-year-old milliner to the stars revealed his creation that bore structural resemblances to pieces worn by Princes Harry and William’s late mother in the past.
From wide-rimmed neutral numbers to floral extravaganzas and polka-dotted beauties, Diana gave the world a show each time she stepped out of a car and onto the Berkshire grass – and Stephen’s latest headpiece is sure to do just that.
Sharing his new work on Instagram, the designer captioned a video of a model wearing the headgear with a note explaining his colour choice and structural thinking. It read: “‘Favourite’ in silver straw and grey taffeta at Royal Ascot Millinery Collective directed by @danielwfletcher @hunt_communications @claridgeshotel @ascotracecourse.”
The hat was a spectacle of harsh angles and height featuring a massive bow in the same silver tone perched on its brim. A tassel in a darker shade of silver hung from the brim and shimmered as the model walked the runway.
© Royal Ascot
© Royal AscotDiana’s collaboration with Stephen
The fashion icon never shied away from turning heads and enjoyed wearing many of Stephen’s lavish creations over the years, including berets and more structured pieces.
During a tour of Wales in 1982, Diana wore her iconic two-toned tan beret, and she chose another one of Stephen’s designs in 1994 when she attended the wedding of Lady Sarah Armstrong-Jones and Daniel Chatto at St Stephen Walbrook in London.
© Getty ImagesHer wedding hat was a midnight-blue, large, wide-brimmed number that featured a ruffled ribbon tied above the brim. The material was tied in a bow and balanced on the back of the rim.
At the time, she wore a navy blazer with white detailing around her lapels and cuffs, and she carried her belongings in a matching envelope-style clutch bag.
© Getty ImagesDuring an event with Stephen attended by HELLO!, the designer opened up about how he approached working with Diana and said: “They have to be light, there has to be an element of fun about them.
“They should tell a story without being this imposing thing. It was definitely about the person who was wearing it, as opposed to the thing you were putting on your head. That was always a guiding light, even if I was doing the craziest hats for Dior or something else.”
The ultimate time capsule collection
Ahead of the opening races at Royal Ascot, the five-day annual event revealed it was launching its 2026 Millinery Collective, a capsule collection of 11 bespoke hats by leading British milliners, including Diana’s favourite Stephen Jones OBE.
The new collection was inspired by Cecil Beaton’s Bright Young Things of the 1920s and 1930s, and claims to reimagine the theatrical era’s romantic modernity through floral headpieces that feature sculptural silhouettes and dramatic veiling.
© Royal AscotRoyal Ascot’s Creative Director, Daniel Fletcher, brought together Rachel Trevor-Morgan, Carol Kennelly, Edwina Ibbotson, Emily Baxendale, Emily Hurst, Filipa Cardoso, Fiona Cooper, Hood London, Jenny Beattie, and Vivien Sheriff to produce the spectacle that is now in its eleventh year.
Daniel explained: “This collection celebrated extraordinary craftsmanship while underscoring millinery’s evolution as a dynamic, contemporary art form. Each designer brings a singular vision and passion to their work, creating a dialogue between tradition and innovation.
“The Collective reaffirms Royal Ascot’s role at the forefront of raceday style, inspiring and shaping the future of summer occasionwear.”
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