“Dressing for Dream Destinations” is a travel series that takes us across the world to daydream about what we’d wear to various locations. (For more, see our past posts on Australia, Russia, India, Morocco, South Korea, Spain, China, Greece, Japan, and the UK.)?

Cuba is an island country with several archipelagos located in the northern Caribbean. The main island is called the Isla de la Juventud. It is only 90 miles away from the tip of Florida. Fun fact: Cuba has one of the highest literacy rates in the world at 99.8% of the population.

Table of Contents

What to Wear in Cuba: Havana

Havana is the largest city in Cuba and its capital with a population of over 2 million people. It is affectionately known as the City of Columns because of the beautiful colonial architecture.

There is no shortage of activities to do in Havana — visit the Museo de la Revolución, take a vintage car tour, walk around Old Havana, and take a stroll on the Malecón.

A bold, off-the-shoulder top is perfect for those Havana nights — especially as temperatures rise. A low-key bag is essential because you will be lugging that around all day as you walk.

Products: Top – Forever 21, Shorts – Forever 21, Bag – Nordstrom, Shoes – Zappos, Earrings – Anthropologie

What to Wear in Cuba: Trinidad

Trinidad is a town in central Cuba and a major player in the tobacco industry. It is the country’s best preserved colonial city that has a unique mixture of 1850s architecture and 1950s cars.

While Trinidad is a major tourist destination, it still maintains a relaxed atmosphere where you can wander around the beautiful plazas, shops, and restaurants.