The Guayabera is a Cuban shirt known for its breathable fabric. With that being said pack breathable materials, dresses and shorts. Also take advantage of ruffles and fun colors and bring a fedora!
The streets are cobblestone and you will most likely do a lot of walking with a taxi here and there. I made the mistake of wearing a pair of Zara espadrilles on one encounter. They were flat and casual but suffered major discomfort after long term walking. Pack WALKING sneakers! Not Vans, Nike’s. I also wouldn’t bother packing heels. Wedges are the way to go for Cuban nights.
What not to wear in Cuba
Any flashy designer items or jewelry. You will look ostentatious and out of place. You also could become a target for opportunistic street criminals.
What I wish I would have packed
Ok ok it was never THIS cold. However my experiences in other Caribbean areas had involved rain of course. To my surprise in Cuba when it rained the weather cooled significantly. This was unlike other Caribbean destinations I’ve traveled where it remains hot and humid. I would have brought items that were long sleeve as well but breathable or perhaps a very light scarf.
What shocked me the most
Fidel Castro propaganda. In the states Cubans and anyone else for that matter are taught to disfavor Fidel. In Florida, the streets flooded with Cubans celebrating his death. However in Cuba you DO NOT speak against Fidel and political issues. He has made his fashion influences on T-shirt’s, on hats, bags and other fashion items everywhere you turn.