The reason why I don't enjoy riding a "traditional" motorbike in heels, though it's quite possible (see below), is because one has to shift gears with one's left foot, and use the rear brake with one's right foot. On older British bikes this may be reversed. Imagine that. To me, this is very awkward to do in heels. On a scooter, there is nothing to do with your feet except look awesome.
I ride around our small town in shorts and mules all the time. This is probably foolish, but I'm 56 years old, and allowed to be foolish, and even the law allows me to be foolish. Yes, I can get a ticket for not wearing a seat belt in a car, but there is no helmet law. And certainly no high heel law. If I have to ride any further than a couple of miles, I wear the proper protective equipment, even if the footwear happens to have an elevated heel.
I got almost zero comments in the Twin Cities. I mean, it's not like Chicago or New York, but it's kind of close to that in being a Big City. People do not say hello when you walk by, they look down. You sometimes have to wait more than 30 seconds at a traffic light. Stuff like that. The one person who did comment on my shoes was a fellow patron at our motel. A young-ish woman of South Asian descent with two small children. I came across her on two different days, and she commented on my shoes at length both times, noting that I had on different shoes than I did before. Other than that, nothing of any note happened, either at the music store or the concert. Ha ha ha.