Apologies to my cousin Diana Taschereau (née Warren) for previously cropping her legend off this photo whose subject eurasian-david has now correctly identified as Dorothy Dransfield. I deferred to Sean Olson's identification of this young woman as his great-aunt, Elizabeth Warnes (née Olson). The Olsons had a much larger trove of family photos and surviving family members to consult than the Warrens. Sean claimed that his photo, taken on the same day, was "one of a set of Elizabeth". I didn't take into account that none of the surviving Olsons had ever met Elizabeth; by contrast the Warrens and the Dransfields had been close friends until Diana left Hong Kong aged nearly twelve in 1938. I consulted a Courtauld Institute expert in the history of fashion to try to date this photo, but the verdict wasn't clear. Maybe someone else would like to have a go.
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Dorothy Dransfield was born…
Dorothy Dransfield was born in 1911. She looks really young here - a mere teenager. I would say this photo was taken in the late 1920s - say 1926-1929 period.
The angle of the sun makes it difficult to say if this was an early morning photo (going to church on a Sunday morning as her father was a loyal member of the Methodist church? Or was this a late afternoon photo and preparing to go to a soirée?) - either way, this street is angled in a roughly east-west orientation. Previous extensive discussion with a better photo showing the buildings behind seemed to have settled on Austin Avenue as the possible location?
Another clue is the big 'V' at the gate. Was this part of a pair of initials of the building? 'V' for 'villa'? Aimai Villas?
Re: Aimai Villas
Unfortunately, the main photo has been cropped and does not show the top of the gate pillar. That said, the pillar itself without the top portion does resemble the pillar at Aimai Villas, Austin Avenue from the 1920s. In another photo, Dransfield is standing beside a car which is believed to have been parked on Austin Avenue outside Aimai Villas. The "V" for 'Villas' on the metal gate is something to keep in mind should there be additional views of the building in the future.