Inspired by the long-standing, UK-based annual international portrait competition, the BP Portrait Award, Rust-en-Vrede Gallery in Durbanville, Cape Town launched the Portrait Award in 2013 – with initial generous sponsorship from Sanlam Private Wealth.

The competition has grown exponentially over the years from a singular prized competition with an overall prize of     R 100 000 to a first prize of R 150 000 and an added second and third prize of R 30 000 and R 20 000 respectively. In 2021 the prize money was sponsored by the Rupert Art Foundation. The Rust-en-Vrede Gallery obtained extra prizes in the form of:

• Ryno Swart Drawing Medal which will be awarded to the best portrait done in a drawing medium as selected by the judges
• Six Zoom sessions with Andrew James, Master Portrait Artist, former Vice-President and member of the Royal Portrait Society in Britain
• The Italian Art Shop Sennelier Watercolour Prize
• The Italian Art Shop Sennelier Oil Prize
• A Faber Castell Drawing hamper sponsored by Pencafe Durbanville

This biennial competition is open to all resident South African artists, 18 years and older, and aims to increase public awareness and appreciation for the art of portraiture, as well as give South African artists an opportunity for further exposure.

 With the launch of a digital entry system for the 2019 competition, it has elevated the standard of South African portraiture for years to come.

The competition is based on anonymous judging: all the works entered are unsigned, thereby levelling the playing field and ensuring that the three judges select the top 100 portraits purely on technicality, narrative and emotional appeal.

Each year, a panel of three judges, consisting of one international and two local judges, select what they deem the best 100 portraits from the entries received. From these, the Top 40, Top 5, Top 3 and winning portrait are selected.

In addition to the Top 40 works exhibited at the Rust-en-Vrede Gallery in Durbanville, the remaining 60 portraits are  exhibited at a venue in Cape Town, under the title PORTRAIT 100, giving the public the opportunity to view 100 of the country’s best portraits in one City. Collectable catalogues are printed to commemorate the Top 40 Portraits.