This is a very good point and could apply to other alternative forms of commuting as well: cycling and walking, for example.
I struggle with this too, so I am eager to read inputs!
How about yoga pants or jeggings instead of jeans, worn under your skirt if it allows it (I'm thinking wider skirts that won't ride up of course)?
As for walking: I walk long distances but can't bring myself to wear heavy running shoes with an outfit that demands pumps. My solution have been to try to buy the most stylish walking shoes; but the caveat is that there is no one-style-fits-all shoe, so I find I am always in need of new expensive walking shoes. Any ideas?
Helmet: I just bought a new bicycle helmet. Gone are the days when you only had one universal type of heavy-duty helmet that dug into your scalp! I tried on some pricier lightweight ones that were much less invasive.
... wonder if the same is true for scooter helmets?
One solution I can imagine for curly/wavy hair: twist strands of hair in curls and secure with pins before putting on the helmet (try also using a hint of hairspray on those strands). Unpin and tousle using wide tooth comb upon arrival.
Here is a problem that arises from cycling to work: sweat. Cyclists, how do you deal with that?
Kristie, You have such a lovely scooter! I would be itching to take it out too! It must be a great style accessory too!