In all honesty, I wear heels every single day of my life and am way more comfortable in heels than I am in flats. I tend to trip over my own feet when in flats and the arch of my foot cramps up. I have high heeled sandals, wedge flip-tops and even high heeled sneakers. I think it just depends on the girl and her comfort in them.
My wife and I always say that every time we go to a theme park we will see a woman in heels, usually rediculous ones. And...........we always see at least one and usually a few hours later carrying her heels wearing brand new flip flops. I have no issue with women wearing them if they are going somewhere for elegant dining.
While we were on the cruise, elegant night was a sight to see. Some women had skyscraper heels on for 10 minute then walking barefoot on the ship. My wife wore 3 inch heels with her dress and wore them for 6 hours until the evening was over and we were back in our room.