From Queen Elizabeth II as a seemingly toothless pensioner, to an apparently semi-naked Prince Philip, royal portraits have not always gone to plan.

Whilst many of the worst have been unofficial, there have been some that were done with the royals' blessing - such as Lucian Freud's controversial 2001 depiction of the Queen.

Yesterday, experts hailed Jonathan Yeo's depiction of King Charles - the first since he became the monarch -as 'the most progressive royal portrait in a very long time'.

The fiery red painting shows His Majesty in the uniform of the Welsh Guards as a butterfly hovers over his shoulder. 

The work has received a much better reaction than Stuart Pearson Wright's official 2003 painting of Prince Philip, which showed the royal bare-chested and with cress growing out of his finger.

Going further back, there has been a chubby Henry VIII and a tiny King James I with his mother Mary, Queen of Scots.  

Yesterday, experts hailed Jonathan Yeo's depiction of King Charles - the first since he became the monarch -as 'the most progressive royal portrait in a very long time'

This slightly abstract depiction of Queen Elizabeth II, from 2006, is called Dreams and Nightmares of the Queen by George Condo.  While you can tell who the subject is, it's perhaps not the most flattering portrayal 

This highly unusual painting of the late Duke of Edinburgh, by Stuart Pearson Wright, shows him bare-chested with strands of cress growing from his finger. The portrait was commissioned by the Royal Society for the Encouragement of Arts, Manufactures and Commerce. Prince Philip declined to go to the artist's studio and instead gave him four one-hour sessions at Buckingham Palace, rather than the suggested minimum of 20

This painting by Canadian artist Andre Durand represented Princess Diana as Pulchinella, the Neopolitan character in the commedia dell'arte. It was commissioned to hang in Da Mario's restaurant in Kensington, one of the late royal's favourite spots, and shows the owner presenting her with a pizza 

This painting of Prince Harry by American artist Elizabeth Peyton is one of many she has produced of the Duke of Sussex and his older brother William 

The depiction of Kate Middleton in a portrait by Jamie Coreth has been slammed for making her look 'frumpy' and 'petulant'

Artist Stella Vine found fame when Charles Saatchi bought her 2013 portrait of Princess Diana, although the late royal's slightly wonky face may have raised eyebrows among fans 

Off with his head! A bizarre painting by artist Stephen Lewis Gilmore depicted King Charles, then the Prince of Wales, as Henry the VIII and showed a beheaded Diana, Princess of Wales. On a locket was a depiction of Camilla

This portrait of Prince William was released by artist John Wonnacott ahead of the Queen Mother's 100th birthday

This painting, by modern artist Peter Sigasby, attracted criticism when it was unveiled in 1991 for being disrespectful to Her Majesty

Not such a masterpiece!  Artist Terry Duffy recreated Botticelli's 'The Birth Of Venus' replacing the heads with Prince Charles, Camilla Parker Bowles, Princess Diana, The Queen and Dodi Al Fayed

Who on earth is that? This representation of the Queen and Duke of Edinburgh by Tai-Shan Schierenberg in 1997 is barely recognisable

This painting, by Kenyan artist Joackim Onyangeo Nedalo, was not particularly well regarded - but had been created from magazine photos and took three months to complete. After the artist, a royal superfan, had finished his masterpiece, he travelled all the way to the Ugandan capital of Kampala, where the Queen was on a state visit, to present the painting

Lucian Freud created this portrait of Queen Elizabeth II as part of the exhibition The Queen: Portraits of a Monarch at Windsor Castle in 2001. The depiction divided both the press and art critics. She is seen with a severe expression on her face, with her features rendered heavily in typical Freud style

A portrait of the late Princess Diana was painted by an unlikely source - Manchester City player Jim Whitley. The portrait was auctioned off in 1998 to raise money for the Diana, Princess of Wales Memorial Fund at the Queen of Hearts Charity Ball in Manchester. Above: Diana's former butler Paul Burrell poses with the portrait

Artist John Ward painted Princess Diana in her wedding dress in 1984, in a portrait that was displayed at the 'Princes as Patrons' exhibition in Cardiff 14 years later

As King Henry VIII neared the end of his life in the 1540s, Flemish renaissance painter Cornelis Massys produced what looks to modern eyes to be a much less flattering depiction of the monarch. It is the earliest contemporary print of an English monarch in the Royal Collection. It was later adapted (above) by another engraver, Peter Isselburg

This bizarre depiction of Emperor Leopold I of the Holy Roman Empire dressed in theatrical costume was produced by Flemish Baroque painter Jan Thomas in 1667

This work by an unknown artist shows Mary, Queen of Scots with her son, the future King James I of England and James VI of Scotland