Michelle Obama and Princess Diana outfits up for auction at New York Fashion Week

Items worn by Kate Winslet and Sarah Jessica Parker form part of lot celebrating pop culture through lens of fashion

Princess Diana's sheep jumper; $50,000 to $80,000. All photos: Sotheby's

Princess Diana's Murray Arbeid evening gown; $80,000 to $120,000

Michelle Obama's 1950s Norman Norell black lace dress; $30,000 to $60,000

Madonna's lace wedding veil she wore on Vanity Fair's Icon Issue Cover 2023; $10,000 to $30,000

Kate Winslet's Givenchy and Alexander McQueen ensemble worn for the 1998 Academy Awards; $30,000 to $60,000

Sarah Jessica Parker's birds of paradise headpiece as seen in Sex and the City; $40,000 to $70,000

Hermes Chai Swift and Ecru Toile Market Bucket Bag; $1,000 to $3,000

Update: Princess Diana's sheep sweater sold for $1.14 million on September 14.

Sotheby's is auctioning several fashion pieces worn by Michelle Obama and Princess Diana – with some expected to sell for six figures.

The Fashion Icons sale runs until September 14, with only 10 items up for grabs. From Thursday, as part of New York Fashion Week, the pieces will be on display at the company's office in the city.

Princess Diana's sheep jumper by luxury British brand Warm and Wonderful is on sale. She wore the piece while watching a polo match of King Charles III, who was then the Prince of Wales, in 1981. It features whimsical black and white sheep motifs.

Princess Diana's sheep jumper. Photo: Sotheby's

There are currently 13 bids for it with the highest offering $110,000, which is significantly higher than Sotheby's estimates of $50,000 to $80,000.

The lot includes two official letters Buckingham Palace wrote to Warm and Wonderful requesting to either repair or replace the piece after it suffered damage. Princess Diana wore it to another polo match in 1983.

A Murray Arbeid evening gown she wore in 1985 is also listed with a guide price of up to $120,000.

Also part of the sale is a black lace dress worn by former US first lady Michelle Obama during a Christmas charity event at the White House in 2010.

Michelle Obama's vintage outfit. Photo: Sotheby's

The 1950s vintage piece, with an estimated sale price of $60,000, is from the late fashion designer Norman Norell, who is often credited as the father of American high fashion. It features a fitted bodice and a mid-length organza skirt, over a petticoat made with layers of tulle.

A 19th-century birds of paradise headpiece, worn by Sarah Jessica Parker in Sex and the City and And Just Like That is also on sale.

The piece, estimated to fetch up to $70,000, was styled for her character Carrie Bradshaw. It served as an alternative bridal accessory, paired with a Vivienne Westwood wedding gown.

The dress Kate Winslet wore to the 1998 Oscars, when she was nominated for Best Actress for her role in Titanic, is also available.

The green silk gown is a custom Givenchy embellished with gold embroidery. The lot comes with a matching bolero by Alexander McQueen. It has an estimated price tag of between $30,000 and $60,000.

Four Hermes bags are also on sale, all of which are part of a private collection by the late American actress Lauren Bacall.

On its website, Sotheby's says the auction “celebrates the legendary people, unforgettable events and unparalleled creativity through the lens of fashion”.