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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.
It is influenced by the cultural diversity that can be found in the various regions of Ecuador and the Galapagos Islands. People who are familiar with the native dress can often tell what region a local is from based on what they wear. You can expect to see many distinctively dressed Otavalenos in Ecuador, especially in the Quito area. The men's dress usually consists of a blue poncho, a fedora, or a felt hat and white, calf-length knickers. The Shimba (a long braid that hangs down nearly to the man's waist) that dates back to pre-Inca times is a very traditional piece of clothing.