Until her mid-teens she wore her hair cut short like a boy's, and by her late teens had articulated a dislike for conventional female clothing. She was much influenced by a family friend, the masculine Sybil Mounsey-Heysham who gave her a model of indifference to etiquette and fashion and a preference for uniforms. She adopted the twenties' fashion of flattening her breasts, and would use a handkerchief to conceal all hint of cleavage.
Robert Baden-Powell, the founder of scouting, then 55, on meeting the 23-year-old Olave on an Atlantic crossing, recognized her purposeful walk as one that he had noted in Hyde Park two years previously. He was attracted by her sporting prowess, and by the fact that the had the same birthday, 22 February. He was able to marry her whereas he had been uncomfortable with the femininity of other women, although he still had severe headaches from shortly after their marriage until he stopped sleeping with her after the birth of their third child.
She was made Dame Grand Cross of The Most Excellent Order of the British Empire (GBE) 1932. In addition Finland awarded her the Order of the White Rose, and Peru the Order of the Sun.
- Tim Jeal. The Boy-Man: The Life of Lord Baden-Powell. William Morrow and Company, Inc. 1989: 85, chp 11.