Sir Cliff Richard turns 86: Iconic pop singer celebrates his big day with a cake and wine as he pulls out all the stops in a PVC snake print jacket

Published: 09:08 EDT, 15 October 2026 | Updated: 09:08 EDT, 15 October 2026 Sir Cliff Richard celebrated his 86th birthday in style on Wednesday as he enjoyed cake and wine on his big day.The iconic pop singer pulled out all the stops for his special moment, slipping into a jazzy snake print jacket in new pictures shared to his Instagram on Thursday.In the snaps, the Summer Holiday hitmaker delightedly held up a glass of wine as he toasted his birthday before blowing out the candles on his cake which was covered in frosting. He was then seen cutting a slice while flashing a broad smile for the camera.Captioning his post, Sir Cliff penned: 'Thank you for all my amazing and thoughtful birthday wishes. I had a lovely day and celebrated with friends (& cake!) It comes after Cliff paid a touching tribute to late close friend Cilla Black as the latest instalment of his iconic annual calendar was revealed. Sir Cliff Richard celebrated his 86th birthday in style on Wednesday as he enjoyed cake and wine on his big day In the snaps, the Summer Holiday hitmaker delightedly held up a glass of wine as he toasted his birthday before blowing out the candles on his cake which as covered in frostingIn August, the singer released images from his 2027 edition, including a shot of him wearing a tie-dye jacket and shorts, and standing at the back of a boat named ‘Cilla’.Sir Cliff and Cilla, who died in 2015 at the age of 72, had enjoyed a close friendship for more than 50 years and they both had holiday homes in Barbados where they spent time together.His latest calendar cover shows the singer, whose many hits include The Young Ones and We Don’t Talk Anymore, depicted on a postage stamp, standing in front of a cruise ship. In one month Sir Cliff is shown lying on a cream sofa, and holding a hardback copy of his first autobiography, It’s Great To Be Young, which he released in 1960 at the ripe old age of 19.Speaking about the calendar, Sir Cliff said: 'My favourite pastimes are travelling and spending quality time with friends and the pictures in the 2027 calendar are a small snapshot of some wonderful times in May and June this year in various locations.'I am delighted to be sharing these with you in my 2027 calendar, of which, I am so proud. It might be a bit early but a happy 2027 to you all.'The pop veteran started releasing a calendar in 1979 and they are thought to have earned him more than £2million.According to Calendar Club, which tracks sales, his 2022 release was the bestselling of any music star’s calendars, beating Harry Styles. The iconic singer pulled out all the stops for his special moment, slipping into a jazzy snake print jacket in new pictures shared to his Instagram on Thursday Captioning his post, Sir Cliff penned: 'Thank you for all my amazing and thoughtful birthday wishes. I had a lovely day and celebrated with friends (& cake!)In 2023, the singer left fans disappointed when he announced that he would be breaking with tradition by not stripping for his calendars going forward.Fans had become accustomed to him posing topless, as he did in a swimming pool in 2022.'I suspect I have done my final topless photo for my annual calendar... it's time to gracefully exit the Chippendales market,' he said.