Items from Amy Winehouse's archives – including handwritten lyrics and a personalised bowling shirt – are being auctioned by Sotheby’s, as part of its inaugural popular culture auction.

Singer Marianne Faithfull is also selling items from her personal collection, including Chanel jackets gifted by Karl Lagerfeld, a signed expired British passport and a black and red artwork of a female figure by Anita Pallenberg dated 1992.

Winehouse’s items are being brought to auction by singer Tyler James, who was one of her best friends.

The handwritten lyrics include Cherry, a hidden track from her debut album Frank, and lyrics to unreleased songs Like Smoke and Knights Before.

"Sharing these items with Amy’s fans is the start of a new journey for me and a new chapter of my life in wanting to help others and give something back," Tyler James said in a statement.

"I know in my heart Amy would wholeheartedly support it."

The red bowling shirt was spotted being worn by Winehouse after a night out in Camden in 2008, and it is embroidered with "Amy Civil", referencing her 2007 - 2009 marriage to Blake Fielder-Civil.

Also being sold is a five-page manuscript, written in black ballpoint ink on white lined notebook paper – it features doodles of hearts, and a doodle of a pin-up girl.

The items are being sold in Sotheby's first pop culture auction, where online bidding will begin from Thursday (29 August).

Katherine Schofield, head of popular culture at the auction house, said she was "honoured to feature two British female trailblazers in our inaugural popular culture sale".

Items being sold by Faithfull include handwritten lyrics for songs from albums including Sleep, There Is A Ghost and Sex with Strangers, an oil painting and tribute to Henrietta Moraes by Maggi Hambling, and scripts from films she’s starred in such as The Black Rider and Marie Antoinette.

Schofield said: "The name Marianne Faithfull is synonymous with a revolutionary time for youth culture and conjures up images of liberation and the epitome of bohemian rock chic.

"To bring items from her personal collection for auction, spanning her songwriting, performance, acting and fashion memories has been extremely insightful and a true privilege and provides an intimate look into the original queen of rock and roll."

There will be an accompanying exhibition in Sotheby’s New Bond Street galleries, in London, from 9 to 12 September.