Generally, everyone dresses casually in Cuba, night clubs, some restaurants, and theatres do require men to wear long trousers and shirts (they can be short sleaved) however, and many hotels have similar dress codes for dinner in the evenings, you can check with one of the love Cuba team to find out if this is the case at your hotel.
The weather is consistently warm in Cuba, even during the off-peak season of May through to October temperatures still hit between 28°C and 32°C, evenings can be a little cooler whilst still pleasant, ladies may wish to bring a shawl especially if they are by the coast. There can be rain during the off-peak months but it’s generally short sharp bursts that last around 5 minutes. It’s a good idea to bring a hat or buy one locally to protect yourself from the sun (you’ll see plenty of Panama hats around) you’ll obviously need swim wear if you wish to enjoy the glorious Cuban beaches or hotels swimming pools, and you should bring some sunscreen.
Comfortable footwear is a must for your holiday in Cuba, wonderful cities like Havana and Trinidad for example are best experienced on foot, and many of the streets are cobble stone lined. If you wish to experience some of Cuba’s world class hiking, you’ll also need suitable shoes for that, and don’t forget your dancing shoes for the evenings!