When it comes to bucking tradition, Princess Diana was one of the best. She didn't really let much hold her back from doing what she wanted to do (for the most part), which is in part why the people loved her as much as they did. And you don't have to just take my word for it! Just check out this clip of the Lady herself shocking her 'handlers' when she decided to run in her son, Harry's, school race as this clip from They_Royals shows!
Click here to watch the video.
Let me set the stage for you. It is Mother's Day, and Prince Harry is at school. Said school is holding a day of events to celebrate the mothers of students, and has invited all of them to come and participate. This, of course, includes Princess Diana who shows up but isn't really expected to participate in much of anything - especially the more physical events.
Naturally, Diana said 'nah' to that and when it came down to a Mother's Day race she decided she wanted to run. One of the royal house's staff explicitly told her that it would be rather uncouth of her to run, namely because she was wearing a skirt and that would be unseemly for a Princess to be seen running in.
So what did Diana do? She pointed out that almost all the other mothers around her were also wearing skirts and that she wasn't that different, then walked down the stairs and onto the field where she joined them all. The race itself, short as it was, showcased her simply flying down the field, skirts akimbo and coming up around her knees, before she managed to get second place.
And did she probably get a few words said to her back at the palace? More than likely - it was pretty unusual for a royal of the court to be seen in such a position, but it was just one more thing that cemented her place in the hearts of so many across the nation and even up to this day!