Here's what Princess Diana's ancestors wore at their respective weddings, including tiaras or flower headbands.
Princess Diana's parents, then-Viscount and Viscountess Althorp:
https://i.pinimg.com/474x/0d/c6/a5/0dc6a56dd9524363a137364fe2378688.jpg
Diana's maternal grandparents, Lord and Lady Fermoy:
https://i.pinimg.com/originals/99/0e/bb/990ebb587c0f69c62c8fadbbffd1dd43.jpg
https://i.pinimg.com/originals/40/5d/9e/405d9e76d1680797ebea84dcc5b65961.jpg
Princess Diana's paternal grandparents, the 7th Earl and Countess Spencer (according to a message board, she wore the flowers on her head instead of a tiara:
https://hosting.photobucket.com/images/ag105/BethBrisbane/9/Tatler%205%20March%201919%20Lady%20Cynthia%20Hamilton%20wedding%20to%20Earl%20Spence,%20then%20Lord%20Althorp%20no%20tiara.JPG
BONUS: Spencer Tiara worn by Cynthia, Countess Spencer (Diana's maternal grandmother). So that makes 6 women who already wore this tiara. Cynthia inherited it from a Spencer relative around 1919, I think.
https://pbs.twimg.com/media/D92Nz_9UcAAknNr.jpg
https://pbs.twimg.com/media/DNNlEV6UMAA1v6G.jpg
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