Kate Middleton's Top Vintage Fashion Moments

Kate Middleton is known for rewearing staple pieces from her wardrobe sometimes a decade apart, which appeals not only to the duchess's thrifty nature but also her values of sustainability.

The wardrobe that Kate took with her on the recent controversial tour of the Caribbean featured many pieces widely celebrated by the fashion press, from a beautiful new ROKSANDA yellow day dress to an elegant ice blue evening gown by Phillipa Lepley. It was, however, the pieces that had a few more miles on the clock that generated the most interest.

On the Caribbean tour Kate not only wore pieces already in her own wardrobe, but also those acquired from others. The duchess debuted three key vintage items of clothing over two days, provoking British Vogue to ask the question: "Is this a new chapter for Kate's wardrobe?"

Though the Caribbean tour featured the most vintage pieces of any other worn in quick succession, Kate has made her eye for vintage clear in previous years.

From Oscar de la Renta and Yves Saint Laurent to chic 1930s handbags and beyond, Newsweek examines Kate Middleton's top vintage fashion moments:

1930s Josef Handbag

The earliest piece of vintage fashion that Kate has worn publicly is a small beaded handbag from the label Bags by Josef.

The brand was a prominent manufacturer of fashionable handbags for ladies during the 1930s through to the 1950s.

Kate Middleton 1930s Handbag
Kate Middleton has worn her circa.1930s Bags by Josef handbag on two occasions. At Wimbledon (L) with Prince William, July 14, 2019. And (R) at the G7 leaders reception, June 11, 2021. VICTORIA JONES/AFP via Getty Images/Oli Scarff /WPA Pool / Getty Images

Kate first debuted this bag at Wimbledon, accompanied by Prince William in 2019. The duchess paired the handbag with a pale blue crepe day dress by designer Emilia Wickstead.

Kate has since worn the bag publicly on one other occasion, at the G7 leaders reception in 2021, hosted at the Eden Project in Cornwall, England. On this occasion she paired the bag with a chic Alexander McQueen coat dress and Aquazzura pumps.

1970s Oscar de la Renta Polka Dot Dress

On an official 2020 visit to Dublin with Prince William, Kate Middleton debuted perhaps one of her most show-stopping vintage items to date in the form of a deep pink and black polka dot mid-length dress with ruffle neckline detail.

Kate Middleton Oscar de la Renta 2020
Kate Middleton wore an Oscar de la Renta design from the brand's 1979 autumn/winter collection to a reception during her visit to Dublin, March 4, 2020. Phil Noble/WPA Pool/Getty Images/

This dress was identified as having come from de la Renta's autumn/winter 1979 collection and won the hearts of users on social media for its resemblance to a dress worn by Princess Diana to the Vatican in 1985.

Kate paired the dress with black accessories from her most relied-upon shoe brand, Jimmy Choo.

1980s Yves Saint Laurent Blazer

Leaving the first stage of the 2022 Caribbean tour Kate surprised royal watchers by wearing a vibrant orange jacket that was revealed to have been in her closet for over 20 years.

Kate Middleton Yves Saint Laurent 2022
Kate Middleton debuted a vintage Yves Saint Laurent jacket on her departure from Belize, March 22, 2022. Chris Jackson/Getty Images

Members of the press covering the royal tour were told that the jacket, which dated from the 1980s, was by designer Yves Saint Laurent and was purchased by Kate in Scotland when she was a student.

On leaving Belize for Jamaica, the duchess paired the jacket with white flared trousers, a mulberry handbag and shoes by Aquazzura.

1950s Printed Day Dress

Jamaica saw the duchess once again wearing vintage, this time purchased more recently from the retailer, Willow Hilson Vintage.

For a visit to Trench Town in Jamaica—marred by a series of PR blunders—Kate wore a turquoise and orange printed dress, which was dated by Willow Hilson Vintage to around 1950.

Kate Middleton Vintage Dress Jamaica 2022
Kate Middleton wore a vintage 1950s printed dress on a visit to Trench Town in Jamaica, March 22, 2022. Chris Jackson/Getty Images/Karwai Tang/WireImage

The duchess had the design slightly altered, with the original spaghetti straps made into more modest shoulder straps from a small matching shawl that accompanied the dress.

1960s Wayne Taylor Handbag

On the second day of her visit to Jamaica, Kate wore a white Alexander McQueen suit with a pop of color in the form of an orange blouse by Ridley London.

The duchess paired this outfit with another vintage item—an orange beaded handled bag also acquired through Willow Hilson Vintage.

Kate Middleton Handbag Jamaica 2022
Kate Middleton carried a Bags by Josef handbag on the second day of her visit to Jamaica, March 23, 2022. Karwai Tang/WireImage/Samir Hussein/Samir Hussein/WireImage

Kate's bag dates from the 1960s and is made of woven raffia with a wooden handle and gold hardware. The bag was originally designed by the now-defunct label Wayne Taylor and manufactured in Japan.

During their tour of the Caribbean, Kate and William visited people and places connected with their Royal Foundation's Earthshot Prize. As this prize is concerned with the preservation of the planet, Kate's efforts to incorporate vintage pieces into her wardrobe have been seen as an extension of this.

Speaking to Vogue, Willow Hilson of Willow Hilson Vintage said that Kate was setting a positive example to encourage people to re-wear vintage and older pieces. "Having someone like Kate wear [our pieces] is just incredible," she said.

"I think she's really trying to be an advocate for reusing and being [more] sustainable. There are still so many people who would never wear second-hand—she can encourage people to be a bit more savvy with their fashion and look for older pieces."

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Kate Middleton Top Vintage Fashion
From Oscar de la Renta to Yves Saint Laurent and 1930s craftsmen, Kate Middleton's wardrobes hold a host of spectacular vintage fashions. Photographed (L) at the airport in Belize, March 22, 2022. And (R) on a visit to Trench Town in Jamaica, March 22, 2022. Samir Hussein/WireImage/Chris Jackson/Getty Images