In many cases tourists come from colder countries in North America and Western Europe to the Caribbean wearing skimpy clothing. Anybody who has visited a popular Caribbean area tourist destination, whether it is Cancun, Mexico, Punta Cana in the Dominican Republic, Montego Bay in Jamaica, or Barbados, will have probably seen heavily tanned tourists in sandals, shorts and vests. With local people, on the other hand, it is often the opposite. While tourists tend to overdress, local people will often be overdressed. For example, many local people may wear long pants rather than shorts in the Caribbean. Professionals may be formally dressed in full suits and long dresses, despite the heat.
What is appropriate to wear depends on where a visitor plans to go in the country they are visiting. If the visitor plans to spend most of their time on the beach, or in an all-inclusive resort, then there is no problem with wearing swimsuits, shorts and sandals all of the time. The only problem that some people may have with the skimpy attire in all-inclusive resorts and beaches, is that they may get sunburned if they have lighter skin.
On the other hand, if a visitor is traveling in areas where locals lives, particularly in towns and cities, then it makes sense to wear more appropriate clothing. There are several advantages to wearing less skimpy clothing. One is that you will look a bit less like an obvious tourist, and are less likely to be hassled. Another is that it is easier to carry things around, like money or a wallet, when you wear more clothing. It is hard to carry a wallet if you are only wearing a speedo and no shirt. If you are wearing jeans, on the other hand, then you have a place to put your stuff. Another benefit is that longer clothing will help to protect your skin from the sun. Longer clothing may also help to protect you from being bitten by insects. Finally, skimpy beach or all-inclusive resort attire may not be considered appropriate in many settings outside of the main tourist areas and resorts. For example, some restaurants or cultural institutions may not allow visitors to come in wearing bathing suits and sandals. In some cases people may be expected to dress in a pretty formal way.
In general appropriate attire for travel in the Caribbean depends on where you are going. If you plan to stay on the beach and in an all-inclusive tourist resort, or in a very tourist oriented area, then the typical ‘tourist’ attire (i.e. bathing suits, shorts, wife beaters, tang tops, and sandals) should be fine. But if you plan to venture outside of the main tourist areas and resorts, then you should probably wear less beach clothing and more street clothing. Beach clothing is appropriate for major resort areas like Cancun, Negril, Punta Cana or some parts of Barbados’ west coast. It would be less appropriate for places outside of the main tourist areas, like Santo Domingo in the Dominican Republic, Kingston, Jamaica or Bridgetown, Barbados.