Judge Sarah Engledow selected the portrait as the winning entry of the $50,000 prize at the Bega Valley Regional Gallery on Friday night.

Dr Engledow, the historian at the National Portrait Gallery in Canberra, said the portrait was “the one that sustained my interest, aesthetically and sympathetically” in a rich field of finalists.

“The whole experience was about ‘spot the difference’,” she said of the two paintings making up the entry.

“I was moved by the restraint of the work, its gentleness, and the effect of its miniscule differences.

“This is the same young man in both paintings - an Australian soldier in uniform of the Boer War or World War One.

“The slouch hat is festooned with emu feathers, characteristics of the Queensland regiments.”

Dr Engledow said that after her first strong reaction to the portrait she then applied her other criteria for assessing a portrait.

“The monochrome work shows the young man in profile.

“The one on the left expresses alertness, and illusion of awareness of a person or thing and on the right there is introspection.

“These differences are barely perceptible, like adjoining frames in a film.

“On the left, one eyebrow hair is sticking straight up and the cocked feathers are slightly more erect.”

Dr Engledow also spoke about the softness of the jaw cut by the hard chinstrap.

“It is soft, plump, young and as a mother of two sons of an age to go to war, as my father did and Shaun Gladwell's father did, I was moved.”

Dr Engledow said it was interesting to see an exhibition that was open to all comers and this particular exhibition was “terrific”.

“It reflects contemporary Australia and the sympathies, interests and lifestyles of a variety of people across the country.”

She was also impressed that three local artists were among the 35 finalists from almost 200 entries.

She said she had spent the last 15 years surrounded by portraits every day, all day, and still her response was primarily whether she would want to hear that person talk, or sit with them in a room.

On a professional level, she looks at the size, the scale of the work, the position of the subject in the frame.

She pays attention to hands, eyes, the application of the paint and if she can imagine the subjects breathing or turning around.

She also looks at whether the sitter is sitting comfortably in that chair and looks carefully at the eyes.

“I don’t go along with the eyes being the windows of the soul – it’s the eyebags and crowsfeet that are the thresholds to the soul,” she said.

Dr Engledow noted  the Shirley Hannan Award attracted artists from all over the country, which was indicative of the great pulling power that was the award’s reputation.

Two artists in this year’s exhibition, Sally Robinson and Matthew Lynn, have work in the National Portrait Gallery in Canberra.

In opening the exhibition, Mayor Bill Taylor paid tribute to Shirley Hannan’s husband, Brian Settle, and the Hannan family for their generosity in sponsoring the award.

“The Shirley Hannan National Portrait Award contributes greatly to the standing of the Bega Valley Regional Gallery as a place of importance when it comes to the arts,” Cr Taylor said.

He said it was wonderful to see so many artists make the journey to Bega for the opening.

He praised the organisational skills of gallery curator Iain Dawson and his predecessor Megan Bottari, the gallery’s new access and learning facilitator Helena Bezzina and the many invaluable volunteers who contributed so much to keeping the gallery functioning so well.

Mr Dawson said the Shirley Hannan Portrait Award had now become one of the most important and coveted art awards in the country.

“I am thrilled with our judge Dr Sarah Engledow’s choice of winner for 2014," Mr Dawson said.

“Shaun Gladwell is one of the country’s most important contemporary artists who represented Australia at the Venice Biennial and was the official Australian war artist in Afghanistan

“To have artists of such high calibre participating in the Shirley Hannan Portrait Award raises the profile of the Bega Valley Regional Gallery to a new level,” he said.

The Shirley Hannan National Portrait Award finalists’ exhibition will continue until July 5 in the Bega Valley Regional Gallery and there will be extended opening hours on the two Fridays, June 6 and 20, to 6pm with a program of events working with the Festival of the Face, and on Saturdays extended hours from 9am until 2pm for the length of show.

A “people’s choice” award of $3000 will be announced at the conclusion of the exhibition.