“Hats give me confidence,” Princess Diana once remarked.
And she wore them with confidence, too, becoming an advocate of lavish headwear.
She consistently pursued millinery in a way that set her apart from other royals.
During Diana’s first years in the spotlight, she primarily wore bird veils to formal occasions, along with brightly colored hats or headpieces with dramatic embellishments.
She later developed a penchant for streamlined designs, wide brims and ’60s-style pillbox shapes.
Kate is also no problem when it comes to hats. Elegant headwear is indeed a talent and she definitely has it.
In fact, the similarities in the two women’s approaches have become more apparent since Catherine became Princess of Wales, with many of Diana’s original looks borrowed from her daughter-in-law – breathing new life into them and giving them a modern twist.
Head to toe burgundy
When Diana stepped out in St Austell, Cornwall, in 1981, she wore a burgundy velvet suit from Jaeger and a pussy-bow blouse, with a matching hat with an ostrich feather designed by John Boyd.
Princess Diana wears a burgundy hat to match her Jaeger velvet suit and a John Boyd hat in November 1983
Catherine, Princess of Wales, visits St. David’s Cathedral wearing a similar burgundy hat and matching coat at St. David’s Cathedral on Friday
Mirroring her view of St David’s Cathedral as she celebrated the first anniversary of Queen Elizabeth’s death, Kate wore a tonal Eponine coat in her usual signature style, topped with a Sahar millinery headdress with bow detail, the had the same slanting curves as Diana. She completed the chic look with a pair of the late queen’s silver jubilee earrings.
Bold blues
Diana paired this sky blue John Boyd pillbox hat and blue heart earrings with a floral dress in Sydney in 1988.
Princess Diana attended a church service in Sydney in 1988 wearing this sky blue pillbox hat by John Boyd
Catherine, Princess of Wales, chose the same bright hue and silk fabric as Diana when she attended Scotland’s National Service of Thanksgiving and Dedication in 2023
We saw this look repeated earlier this year when Kate chose the same bright hue and silk fabric for Scotland’s National Service of Thanksgiving and Dedication, which marked the Scottish coronation of the monarch.
She put her own spin on the hat style, adding an ornate feather to her Philip Treacy hat to match her Catherine Walker coat. The Princess of Wales also wore pearl earrings and a pearl bracelet that once belonged to Diana.
Ladies in red
Diana made a stunning appearance at Nicholas Soames’ wedding in 1981, a few months before her own wedding to Charles.
She opted for a red high-neck dress with a white and blue print by Catherine Walker and a matching red saucer hat by John Boyd.
Kate wore a wide-brimmed Philip Treacy hat at the same pointy angle, elegantly complementing her Alexander McQueen dress at Royal Ascot in 2023.
Diana pictured at Nicholas Soames’ wedding in London in 1981 wearing a red saucer hat by John Boyd
Kate repeated the look this year with a Philip Treacy hat at Royal Ascot
Partnership in teal
While on tour in Wellington, New Zealand in 1983, Diana wore a John Boyd silk hat with fan corsets and dyed it to match her peplum jacket and skirt.
Strikingly similar: Kate was teal from head to toe on St. Patrick’s Day this year. For the occasion, she wore a Catherine Walker coat dress with sharp shoulders, a mock turtleneck, long sleeves and large buttons down the front.
She paired it with teal Gianvito Rossi suede pumps and a matching Jane Taylor London fedora with a dramatic pleated chiffon embellishment.
Diana chooses a teal suit and matching hat for Wellington, New Zealand in 1983
Kate’s look for the 2023 St. Patrick’s Day Parade at Mons Barracks was strikingly similar in color and detail
Veiled detail for a funeral
For the funeral of Adrian Ward-Jackson, former governor of the Royal Ballet, in 1991, Princess Diana chose a wide-brimmed hat with veil details. She paired the extravagant headdress with pearl earrings as well as a black jacket and belted skirt.
At Queen Elizabeth’s funeral in 2022, Catherine replicated Diana’s look, right down to the same pearl earrings and veil details on her Philip Treacy hat.
She turned to her favorite British designer, Alexander McQueen, for a coat dress that would make her pearl necklace – which Diana had previously worn in 1982 – stand out.
Princess of Wales wore a wide-brimmed hat with veiled details to Adrian Ward-Jackson’s funeral in 1991
Catherine, Princess of Wales, at Queen Elizabeth’s funeral in 2022. She took cues from Diana’s funeral ensemble with a 2023 version with a wide brim and bias, giving her a current yet chic look
Electric blue
At the 1985 Children of Courage Awards, Diana appeared in an embroidered bright blue suit by Caroline Charles with a matching hat by Philip Somerville.
Hat maker Somerville often made hats to match the princess’s outfits and was also behind Diana’s switch to Jackie Kennedy-style pillboxes.
Catherine repeated the look when she wore her signature style in the same eye-catching hue on Easter Sunday 2023, bringing back a bright royal blue tailored coat from Catherine Walker that she had worn the year before.
Her matching Lock & Co pillbox hat was accessorized with a thin, oversized bow and she completed the look with some sapphire and diamond earrings.
Princess Diana wore a bright blue pillbox hat with a matching Caroline Charles suit to the 1985 Children of Courage Awards
Princess Catherine replicated Diana’s look when she wore her signature style in the same striking hue on Easter Sunday 2023
Country chic
Diana was the first to wear a fedora – seen visiting Sandown Racecourse in 1981, teamed with a ruffled collar shirt and carrying a Gucci bag.
Kate would later adopt a similar look for a church service in Balmoral in August 2023.
The Princess of Wales looked effortlessly chic in a beige tartan Marlborough trench coat from Holland Cooper and her Hicks & Brown hat with pheasant feathers on the ribbon.
Princess Diana wearing a fedora hat and matching tweed at Sandown Racecourse in 1981
Kate updated the fedora look by adding pheasant feathers to her Hicks & Brown hat in August
Monochrome tilt
When Diana visited the American National Gallery in Washington in November 1985, she accessorized her Catherine Walker suit with a Freddie Fox hat. The hat was worn slanted across her face and had black detailing that perfectly matched the lapels of her tuxedo jacket.
There was a sense of déjà vu at the Order Of The Garter Service in 2023 as Kate embodied Diana’s style in a custom Alessandra Rich polka dot midi dress and a black Philip Treacy hat worn at the same angle and sporting the same spotted print as had her dress. Kate’s ensemble was completed with Diana’s pearl earrings.
Diana’s monochrome outfit, complete with a tilted Freddie Fox hat with feather detail, was an eye-catcher when she visited the National Gallery in Washington in November 1985
Kate’s monochromatic look, complete with feather-detailed Philip Treacy slanted hat, looked like an updated version of Diana’s showstopper at the Garter Service earlier this year
Timeless in black
In 1982, Diana arrived at the National Service of Remembrance dressed in a black blazer, black skirt and black hat decorated with feathers.
Kate took a more modern approach for the St. David’s Day Parade in March 2023, with a single feather on her black Juliette Millinery headdress.
She wore a red Alexander McQueen coat, but like the former Princess of Wales, Kate sported a black funnel neckline and wore her elaborate headpiece at the same angle along with subtle silver earrings.
Diana, Princess of Wales, visits the Cenotaph in 1982
Catherine, Princess of Wales at the St. David’s Day Parade in March