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One thing you need to remember is that casual dressing in Cuenca is a part of life. Jeans, casual slacks, jogging pants, etc. are worn day and night and are acceptable for both men and women. I have seen very few skirts, although I brought a couple. You never know when you might need one.
I'm sure Cubans dress up to go out at night, but what do they wear around the city during the day? Here in Costa Rica, even when it's super hot, in the cities people wear pants and closed shoes. If you walk around in shorts or a dress with flip flops you will stick out. It's also almost considered rude to go into banks with shorts and flip flops on.