Jennie Churchill did not own a tiara of her own till her second marriage to her son Winston's exact age George Cornwallis West... a group of friends then joined to give her a very high diamond and pearl scroll tiara
Clementine was the maternal grand daughter of the Earl of Airlie a very well connected but not wealthy Scottish peer so there may have been a tiara to borrow there...her uncles widow Mabell ?Countess of Airlie (herself an Earl's daughter) had several at her disposal as a lady in waiting for decades to Queen Mary
I finally managed to find 2 descriptions of Clementine Churchill's headdress for her wedding in September 1908.
She did not wear a tiara or any jewels.
It is possible to make out the "Greek band" as well as the effect created by the orange blossoms in some of the photos below. It is a shame that I have not been able to find any good quality photos.
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