I just spent eight days on the road with my skirts. I was in airports, on planes overnight, and in a big city tooling around. I was worried that I might feel limited by my skirts project, but I think it actually made traveling easier.
When I packed my suitcase I had plenty of room because the skirts don't take up much space, and because I only had 4 bottoms with several tops for each one. Everyday I could easily choose and outfit and get dressed without much fuss. In a big city sometimes pants/trousers don't look stylish enough, but a skirt almost always has the little extra style that looks dressed up. (You can usually add small accessories like a fancy top, a scarf or jewelry to make it look more so.) I admit that I was not as chic as many of the women I saw, but I was also not as out of place as the tourists in their jeans and athletic shoes.
As I found out this past winter, it is definitely possible to stay warm enough in a skirt, and it is even easier to stay cool. The weather last week was partly sunny, partly rainy and I could see by my husbands trousers that I was better off in a skirt because his pant legs got soaked at times. I had a raincoat and an umbrella but there was one day when I wish I would have had some wellies. While packing, I had to make sure that I had style while taking care of the comfort of my feet, and there was only so much room in my one bag. I am always struggling (and failing mostly) to find the perfect accessories for the very bottom (the so called "foot") of my outfit.
This leads me to my other obsession and possibly a cause for a future year long project -
shoes ... but that is another story altogether!