Skip to main contentSkip to footer

30 vintage Royal Ascot photos to inspire your race day style

Use these incredible looks for your 2024 Royal Ascot fashion inspo...

30 vintage Royal Ascot photos to inspire your race day style© Hulton Archive
Lauren Ramsay
Online Writer
Updated: June 19, 2024
Share this:

Sign up to HELLO! Fashion for style tips, cultural insights, must-have items, and more

By entering your details, you are agreeing to HELLO! Magazine User Data Protection Policy. You can unsubscribe at any time. For more information, please click here.

Royal Ascot is the Paris Couture Week of the British social season. Arguably the most fashion-forward event of the summer, the annual five-day festival perfectly combines the excitement of horse racing with a dress code that is more strict, yet brings more extravagance than any other.

Each year we look forward to seeing what the stylish socialites, the VIPs of the Royal Enclosure, the chicest celebrities and of course we have always looked forward to see what the British Royals would be wearing.

Since the event began in 1911, Ascot fashion has always stuck to the sartorial rules that still stand today and haven't changed much overtime. But the way guests have adhered to the dress codes has constantly reflected trends of their time. From fur and pearls in the 1920s, to pared back looks during the 1940s thanks to fabric rationings after WW2, to bright colours of the swinging 1960s, an elegant take on the boho movement during the 1970s, all the way up to 2017, when Saville Row tailor Daisy Knatchbull reportedly became the first woman ever to wear a morning suit.

In 2023, it wasn't just guests who will be altering their dress agendas. Ascot's official Style Guide itself took a new direction. Renamed the 'Royal Ascot Lookbook 2023', it consisted of six different fashion edits: Luxe, Tailoring, Pre-Loved & Rental, Vintage, High Street and Emerging Designer.

MORE: 5 Ascot 2023 outfit ideas that are actually pretty major 

RELATED:  The History of Ascot Fashion from 1711 - 2023

Luke Jefferson Day, the stylist who worked on the 2023 lookbook said, “I wanted to encourage unexpected freedom, under the guidance of the enclosure dress codes, and inspire racegoers to be a little more unconventional and inventive in the way they dress up, and how they source their looks. [...] I want to excite people to think outside of the box – whether that be shopping resourcefully on the high street or by being more eco-conscious through hiring a look or finding a rare vintage gem.”

Still not sure what you're wearing? Hello! Fashion have put together five unbelievably chic outfits that are pretty major in every way, shape or form.

The 30 best Royal Ascot photos of all time:


Mrs Liddel-Hart© Hulton Archive

Mrs Liddel-Hart

At Royal Ascot, Captain and Mrs. Liddell-Hart showcased the vivid fashion of the early 19th century. Mrs. Liddell-Hart wore an elegant, fitted jacket with puffed shoulders, a high lace collar, and intricate ribbon details. She accessorised with a stylish hat adorned with feathers and ribbons, a matching parasol, and a small handbag, epitomising Edwardian style.


14th June 1949:  Miss Sondra Ritter of New York arrives on the first day of Royal Ascot in Berkshire carrying a novelty transparent perspex vanity bag.  (Photo by J. A. Hampton/Topical Press Agency/Getty Images)© J. A. Hampton

Sondra Ritter

Miss Sondra Ritter made a striking entrance on the opening day of the 1949 Royal Ascot, carrying a unique transparent perspex vanity bag that turned heads and set a trend.


Elizabeth Taylor© Keystone

Elizabeth Taylor

On June 14, 1950, actress Elizabeth Taylor, accompanied by her first husband Conrad Hilton, were spotted at the Savoy Hotel, London, en route to Ascot. Elizabeth wore an exquisitely tailored jacket featuring a wide, structured collar and buttons. Her ensemble was completed with a stunning wide-brimmed hat adorned with floral decorations.


On the first day of the Royal Ascot meeting, model Fiona Campbell Walter (later Baroness von Thyssen) wears a black straw hat, a white corded suit and pearl necklace and is carrying a fur stole.  (Photo by Keystone/Getty Images)

Fiona Campbell, 1953

In 1953, model Fiona Campbell Walter (who later became Baroness von Thyssen) wore an intricately embroidered white two-piece suit. Giving the look extra elegance, she paired it with a pearl necklace, a black straw hat and carried a fur stole.  


Marie Helvin and Jerry Hall, 1982© Kypros

Marie Helvin and Jerry Hall

Fashion icons Marie Helvin and Jerry Hall made a stunning appearance at the Royal Ascot, showcasing their impeccable style.  Helvin dazzled in a sophisticated black dress, accentuated by a white jacket draped gracefully over her shoulders. She accessorised with a string of pearls and an exquisite brooch. White lace gloves completed her look. Jerry Hall wore a striking black jacket with contrasting white lapels and piping, paired with a black skirt. The jacket, featuring gold buttons, added the signature dose high-octane 80s glamour to her look.


17th June 1952:  Princess Margaret (1930 - 2002) is driven to the opening meeting of the Royal Ascot horse-racing event near Windsor in Berkshire.  (Photo by Fox Photos/Getty Images)© Fox Photos

Princess Margaret

Princess Margaret graced the opening day of the Royal Ascot in 1952, exuding elegance and charm. Her sophisticated attire, accentuated with a stunning pearl necklace and her exquisite brooch, made the royal a highlight of the event.


LOS ANGELES - DECEMBER 24: Wilfrid Hyde-White as Colonel Hugh Pickering and Audrey Hepburn as Eliza Doolittle in "My Fair Lady".  Original release date December 25, 1964.  (Photo by CBS via Getty Images) © CBS Photo Archive

Audrey Hepburn

Audrey Hepburn made an unforgettable appearance at Ascot as Eliza Doolittle in the 1964 film My Fair Lady. She dazzled in an opulent ensemble featuring a striking white gown adorned with intricate black and white lace detailing. Her outfit was further elevated by a large, dramatic hat embellished with black ribbons and flowers, perfectly capturing the essence of Edwardian elegance. The stunning costume, not only highlighted her character’s transformation but also became one of the most iconic looks in cinematic history.


Prince Rainier of Monaco and Princess Grace Kelly attending the Royal Meeting at Ascot, Berkshire, June 14th 1966. (Photo by Central Press/Archive Photos/Getty Images)© Central Press

Princess Grace Kelly

Prince Rainier of Monaco and Princess Grace Kelly attended Ascot on June 14th, 1966, epitomising royal sophistication. Princess Grace dazzled in a chic, floral-patterned dress elegantly accessorized with a classic string of pearls and stylish dark sunglasses. She completed her outfit with a broad-brimmed white hat, which provided a striking contrast to her dress, and a sleek handbag.


Mrs. Gerald Legge, later Countess Spencer, and stepmother to Diana, Princess of Wales, wears a large hat decorated with cherries at Ascot. (Photo by © Hulton-Deutsch Collection/CORBIS/Corbis via Getty Images)© Hulton Deutsch

Raine Spencer

Mrs. Gerald Legge, who would later become Countess Spencer and stepmother to Diana, Princess of Wales, made a memorable appearance at Ascot wearing a show-stopping ensemble. Her large, stylish hat, adorned with vibrant cherries, was the highlight of her outfit, capturing the attention of onlookers. She paired this unique headpiece with a matching handbag, making her one of the standout fashion icons at the event.


Tandy Cronyn, Ascot 1968© Mirrorpix

Tandy Cronyn

In June 1968, actress Tandy Cronyn made a rather sensational appearance at Royal Ascot. Her outfit was a bold statement piece, covered entirely in vibrant, colorful flowers. She wore a matching set of floral-adorned knickers, a wide-brimmed hat, and stylish shoes, all coordinating with the flower theme. The ensemble was complemented by a parasol, also decorated with flowers... naturally.


Gertrude Shilling, Ascot 1969© Hulton Archive

Gertrude Shilling

On June 20 1969, Gertrude Shilling captivated onlookers with her stunning and extravagant outfit. She wore an apricot-coloured ensemble adorned with feather trim, exuding elegance and flair. The highlight of her attire was an enormous, matching cartwheel hat. The hat made a bold fashion statement, ensuring she stood out as one of the most memorable figures at the event.


Nina Baden-Semper, 1972© Victor Drees

Nina Baden-Semper

In 1972, actress Nina Baden-Semper graced the scene in an exquisite light beige full-length dress. The dress featured elegant pleats throughout, including the sleeves. Floral pom-poms adorned the dress, providing a whimsical detail. Nina completed her look with a floppy hat, trimmed with matching floral accents.


Queen Elizabeth II, 1973© Princess Diana Museum

Queen Elizabeth II, 1973

In 1973, Queen Elizabeth II made a stylish and memorable appearance at Royal Ascot. She wore a striking, light green coat dress, tailored to perfection with a gently flared silhouette and large, elegant buttons. The coat dress featured a wide, notched collar. Her ensemble was enhanced by her green headpiece, adorned with white floral appliqués. The Queen completed her look with white gloves and a matching handbag, exuding regal poise.


The Prince and Princess of Wales in the royal enclosure at Royal Ascot, June 1986. Princess Diana wears a cream peplum jacket and somerville hat© Getty

Princess Diana, 1986

In 1986 Princess Diana wore the chicest cream peplum jacket and skirt two-piece paired with a matching choker necklace and wide-brimmed hat.


Diana, Princess of Wales attended Ascot race meeting in England, wearing a black and white spotted dress by Victor Edelstein and a Philip Somerville hat, June 1988.  © Princess Diana Archive

Princess Diana (again), 1988

In June 1988, Diana, Princess of Wales, captivated the crowd at the Ascot in chic black and white spotted dress by Victor Edelstein. The dress featured a fitted bodice, a cinched waist, and a full, flared skirt. To match her dress, Diana donned a stylish hat by Philip Somerville. Crafted in a matching black and white palette, it featured a wide brim and elegant detailing, perfectly balancing the bold pattern of her dress.


Princess Beatrice of York attends Ladies Day of Royal Ascot 2017© Getty

Princess Beatrice, 2017

In 2017, Beatrice schooled us in colour blocking for the races in a powder blue dress with black detailing. Her mother, Sarah Ferguson, then wore the same dress just a month later - talk about mother/daughter fashion goals...


Daisy Knatchbull, 2017, Royal Ascot

Daisy Knatchbull

In 2017, Daisy Knatchbull, the founder of The Deck, made a bold and stylish statement at Ascot by donning tailored menswear. She wore a sharp black morning coat, paired with a light blue double-breasted waistcoat that added a touch of pastel elegance. The morning suit homage was completed with grey pinstriped trousers. Daisy's outfit was impeccably accessorised with a classic top hat, a cream-colored shirt, and a subtle tie, showcasing her attention to detail and commitment to traditional menswear elements. She added a feminine twist with a pair of stylish heeled sandals, adorned with floral embellishments.


Meghan, Duchess of Sussex, 2018© Karwai Tang

Meghan Markle

In 2018, Meghan Markle, the Duchess of Sussex, attended Ascot in a stunning white Givenchy shirt dress. The elegant, asymmetrical hemmed dress was cinched at the waist with a sleek black belt. She accessorised with a dramatic black and white Philip Treacy hat, black pumps, and a matching clutch, epitomising modern royal.


ASCOT, ENGLAND - JUNE 18:  Emma Weymouth attends day 1 of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by David M. Benett/Dave Benett/Getty Images for Ascot Racecourse)© David M. Benett

Emma Thynn

Emma Weymouth-Thynn, Marchioness of Bath, attended the first day of Royal Ascot on June 18, 2019, in an elegant light powder blue ensemble. She wore a sophisticated coat adorned with delicate embroidery and feather-trimmed sleeves. Emma accessorised with a striking pastel hat featuring intricate loops and a pair of chic, matching pointed-toe heels.


ASCOT, UNITED KINGDOM - JUNE 18: (EMBARGOED FOR PUBLICATION IN UK NEWSPAPERS UNTIL 24 HOURS AFTER CREATE DATE AND TIME) Lady Kitty Spencer attends day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Max Mumby/Indigo/Ge© Max Mumby/Indigo

Kitty Spencer

Lady Kitty Spencer graced day one of Royal Ascot on June 18, 2019, in an exquisite white lace dress featuring delicate flutter sleeves and a form-fitting silhouette, flaring out subtly at the hem. She accessorised with a chic, sculpted white hat adorned with a black feather, a sleek black clutch, and elegant sheer black heels, blending classic elegance with contemporary style.


 Catherine, Duchess of Cambridge attends day one of Royal Ascot at Ascot Racecourse on June 18, 2019© Getty

Princess Kate, 2019

The Princess of Wales perfected vintage glamour in a powder blue Elie Saab top and skirt set, boasting a pussybow tie, sheer embellished sleeves and lace panelling. 

Four years later for a garden party at Buckingham Palace in May 2023, she recycled the exact same outfit, proving the timelessness of such a look.


ASCOT, ENGLAND - JUNE 19: Sabrina Percy on day 2 of Royal Ascot at Ascot Racecourse on June 19, 2019 in Ascot, England. They were commissioned by Ascot Racecourse to paint benches to be positioned by the track in the Royal Enclosure. Each girl interpreted© David M. Benett

Sabrina Percy

On June 19, 2019, Sabrina Percy attended day two of Royal Ascot at  in a striking white dress with a square neckline and long sleeves. She accentuated her waist with a bold black belt and accessorised with a matching black handbag. Finishing off her look, she wore a stylish black and white boater hat and a sheer black neck scarf.


ASCOT, ENGLAND - JUNE 20: Tatiana Korsakova attends Ladies Day at Royal Ascot Racecourse on June 20, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images for Tatiana Korsakova)© Chris Jackson

Tatiana Korsakova

Tatiana Korsakova dazzled on Ladies Day at Royal Ascot on June 20, 2019, in a stunning mint green ensemble. She wore a sleek dress paired with an elegant, matching cape coat. Her look was accentuated by a unique headpiece with oversized bow and a white novelty cloud purse. Delicate heels completed her sophisticated and eye-catching outfit.


Kate Middleton at Ascot© Samir Hussein

Princess Kate

On June 17, 2022, the Princess of Wales, graced Royal Ascot in a stunning polka dot dress. Kate's elegant white dress, adorned with brown polka dots, featured a high neckline and long sleeves, exuding timeless sophistication. She accessorised with a chic brown and white hat adorned with floral details, brown suede heels, and a matching clutch.


Princess Beatrice, 2022© Karwai Tang

Princess Beatrice

On June 18, 2022, Princess Beatrice of York attended day five of Royal Ascot at Ascot Racecourse in a charming black and white polka dot dress. The dress featured puffed sleeves and was adorned with bow embellishments along the front. She accessorised with a stylish black and white fascinator, a black handbag, and elegant black heels.


Maya Jama, 2022© Karwai Tang

Maya Jama, 2022

On June 14, 2022, Maya Jama turned heads at Royal Ascot with her vibrant pink floral dress featuring multiple tiers of ruffles and a high neckline. Completing her look, Maya accessorised with an intricate, matching fascinator adorned with elaborate floral details, adding a striking touch to her standout outfit.


Kate Waterhouse, 2022© Kirstin Sinclair

Kate Waterhouse

On June 18, 2022, Kate Waterhouse attended Royal Ascot in a black tailored jacket with dramatic shoulder pads and a white wide-collared shirt, paired with a pleated white midi skirt. Her look was accessorised with a chic veiled beret, gold clutch, and black heels.


ASCOT, ENGLAND - JUNE 15: Georgia Toffolo poses during Royal Ascot 2021 at Ascot Racecourse on June 15, 2021 in Ascot, England. (Photo by Kirstin Sinclair/Getty Images for Royal Ascot)© Kirstin Sinclair

Georgia Toffolo

On June 15, 2021, Georgia Toffolo attended Royal Ascot in a captivating pastel blue dress that featured dramatic puffed sleeves and an oversized bow at the back, creating a stunning silhouette. She accessorised with a floral headpiece, pearl earrings, and a white ruched handbag, completing her look with Amina Muaddi heels.


Hana Cross, 2022© Samir Hussein

Hana Cross

On June 16, 2022, Hana Cross attended Royal Ascot in a vintage-inspired ensemble. She wore a Alessandra Rich floral dress with puffed sleeves and a deep V-neckline adorned with a oversized collar and a black ribbon tie. Hana completed her look with a dramatic black fascinator featuring a veil, and stylish black T-strap heels.


Zenouska Mowatt, wearing Jane Taylor, attends Royal Ascot 2022 at Ascot Racecourse on June 15, 2022 © Getty

Zenouska Mowatt, 2022

Princess Alexandra's granddaughter, Zenouska Mowatt, wore a timeless powder blue dress with chiffon sleeves in 2022 which she paired with a similar hued headpiece by Jane Taylor. Bold blue court heels and a matching clutch bag made her look stand out from the crowd.

More Hello! Fashion

See more