When he was 15, upon the completion of his education, Raeburn was apprenticed by James Gilliland, a goldsmith. During this period, the artist executed drawings on ivory by his hand, which would be used in pieces such as mourning rings and several pieces of jewelry. Many of these objects still exist.

Soon, Raeburn started to produce highly finished miniature portraits, which were warmly received by critics and patrons alike. The artist would promptly expand towards oil painting, a technique that he was self-taught.

Gilliland was rather pleased, as well as interested in his pupil's rapid development. He soon introduced the young artist to Scottish painter David Martin, who was Allan Ramsay, the Latter's assistant, as well as the first artist to make a living out of portrait painting in the city of Edinburgh.

Around 1780, Raeburn married Ann Leslie, a widow twelve years older than him, who was quite stable financially, as well as having several properties. Henceforth, Raeburn became an artist with independent means.

Since at the time was a tradition that young artists would travel to Rome, the newly-married couple would promptly set off to Italy. Passing through London, Raeburn was kindly received by distinguished English painter Sir Joshua Reynolds, who was the president of the Royal Academy. Reynolds also advised the artist on where and what to study in Rome, especially Michelangelo's oeuvre.

Now at the Italian Capital, Raeburn made acquaintances with Pompeo Gerolamo Batoni, fellow Scot painter Gavin Hamilton, and an antique dealer named Byers, who gave the artist several useful tips. Following two years of study in Italy, Raeburn returned to Edinburgh, where he would begin a very successful career as a portrait painter.

Although a respected artist from the United Kingdom, Raeburn did not establish many contacts in London, only exhibiting at the city a few times. He considered moving south, following the death of his friend John Hoppner. However, the artist rejected the prospect of living in the sophisticated and yet troublesome life of the metropolis. From this period on, Raeburn exhibited regularly at the Royal Academy.

When David Martin died in 1797, Raeburn became the most fashionable portrait painter in Edinburgh.

King George IV knighted Raeburn during one of his visits to Scotland. He also appointed him as an official painter for Scotland, as well as King's miniature portraitist, or Limner.

Sir Henry Raeburn died in July 1823, in his beloved Edinburgh.