I've done plenty of stupid things over the years, but the most painful lesson I learned was to never wear couture heels while travelling.
I had a new pair of super high, super skinny heeled Jimmy Choo sandals. I was so proud of them, they were gorgeous with their brown suede and gold leather trim so I just had to wear them for my trip.
I ended up running late, and literally had to run for my plane. You can imagine how well this worked out, with a jacket, suitcase, purse, laptop bag, etc... my super fancy heel got caught in a crack and I ended up faceplanting on the floor.
NEVER AGAIN. I still love my Jimmy Choos, but the heels stay in my suitcase and I wear flats or low, wider heels for the trip