The show at Kirkcaldy Galleries in Fife will include 12 oil paintings he produced in his early 20s and 30s, signed with his birth name, Jack Hoggan.
The works, painted before he achieved international success in the 1990s, will go on show alongside pieces that have sold for five and six-figure sums.
It will be the artist’s first retrospective since a major show at Kelvingrove Art Gallery and Museum in Glasgow in 2013, and the first to focus on his formative years and early career.
Vettriano, from Fife, left school at 15 to become a mining engineer but took up painting after a girlfriend gave him a box of watercolours for his 21st birthday.
The artist, born in 1951, learned by copying the Old Masters, Impressionists and Scottish artists and drew inspiration from works he saw in Kirkcaldy Galleries, which is managed by cultural charity OnFife.
He said: “I grew up admiring the work of so many great Scottish painters in what was then my local gallery.
“Kirkcaldy has a great permanent collection and a free admission policy, so I have the Galleries to thank for the start of my art education.”
The new exhibition, which opens in June, will include one of two paintings Vettriano entered for the Royal Scottish Academy’s annual show in 1988.
Both paintings sold on the first day, a turning point that inspired him to become a full-time artist.
Among the 57 private loans will be pieces such as Billy Boys, Valentine Rose and Bluebird at Bonneville.
OnFife exhibitions curator Alice Pearson said: “This is the first time Jack has agreed to exhibit work painted simply as a hobby beside later pieces that wowed sell-out shows in London and New York.
“The exhibition will highlight the diversity of subject matter and styles Jack tackled while learning his craft, giving him the confidence and technical ability to develop his own identifiable style.”
Also included will be Long Time Gone, which is set against a backdrop of the now-demolished Methil power station, a once familiar Fife landmark.
The exhibition was originally planned for 2019 but has twice been postponed because of Covid-19 restrictions.