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Walking and bus tours in Old San Juan and forests in Puerto Rico.

Telephone:  +1-787-605-9060    Fax:  +1-787-946-9060     E-mail:  info@legendsofpr.com


What to wear in Puerto Rico:  "Dressing for a fortress city"

Debbie Molina-Ramos
Debbie Molina-Ramos
Tourist Guide

The ideal attire for walking in the fortress city of Puerto Rico is wearing a pirate outfit!  Just kidding.

Here's some real advice on what to wear in Old San Juan so you can enjoy the experience.

  • A brief historical background

Christianity was brought down from the Spanish Conquistador, it has influenced how most Puerto Rican dress. Upon the arrival of the Protestants in 1898, conservative dressing was more noticeable.

Puerto Ricans take pride on how they dress.  They pay close attention on the ethics of dressing for all occasions. Style is very important to them. Northerners looks forward to feel the warmth of the sun on their skin and enjoy walking around shirtless on the cobblestone streets of Old San Juan and women showing their bikini top. The locals do not approve on this type of dressing.  They would prefer people to wear sleeveless shirts. This is an alternative for travelers looking to enjoy the tropical weather with the least amount of clothes.

It was shocking for the Europeans to see the Taíno, native inhabitants of Puerto Rico, walking around naked. Why wear clothes in a tropical island? Men, children and teenagers of both sexes walked around naked.  Married women walked topless and wore “naguas”, a cotton skirt in which length indicated their social status.  The Chief’s wife wore their “naguas’” down to the ankles and the married women wore theirs below the knee. Adults painted their skin and wore necklaces, earrings, bracelets and pendants made of bones and rocks on their nose.

During the “Areytos”, religious ceremonies, the Taíno would dress by painting their body with red paint, wore parrot feathers, jewelry made out of sea conch, corrals and gold pendants. The chief and “bohiques”, upper class,  wore caps decorated with feathers.

The Spanish Military would send their soldiers to the town of Cayey prior to their posts at the forts in San Juan, so that their bodies can adapt to the tropical weather.  At the actual forts you will be able to see and learn about the uniforms worn by the soldiers during four centuries.  The United States Army, instead, send their soldiers directly to the forts and plant Australian pine trees to provide shade.

The slaves brought West and Central African culture and traditions to Puerto Rico. Tribes and countries that shaped Puerto Rico's African heritage were the Yoruba, Ashanti, Bantu and Congo.

Slaves were clever in the way they worshiped their gods.  They disguised them with the Catholic’s religious symbol. For example, the multiple colored candles used today by the Puerto Ricans was designed by them.  Each color represented one of their African gods.

bomba dancefocloric dance

They also created their own fashion by modifying the Spaniard-style of dressing to their unique style.  The most known clothing can be seen during a folkloric dance known as “bomba”.

Puerto Rican crafted jewelry
The article about Puerto Rican arts & crafts mentions 26 types of craftsmanship made in Puerto Rico and most of them are functional.

Many Puerto Ricans at all ages, whether male or female, wear custom-crafted necklaces, earrings and bracelets on a daily basis.

Dress up and enjoy your San Juan Nights with a rum tasting and dinner tour.


Here are several tips when deciding what to wear in "My Old San Juan":

  1. Be part of the culture; consider wearing accessories such as a necklace and earrings set made by a local artisan.
  2. When making your restaurant reservations do ask about the dress code.  Many restaurants do not accept shorts, jeans, sleeveless shirts or T-shirts or other inappropriate attire.
  3. Men are required to remove their hats when entering a church facility.
  4. Puerto Rico’s season consist of 6 month of rain and 6 month of dry weather. Wearing sandals on a rainy day is ideal, because the air will dry the feet.  On the other hand, wet socks have to be changed. Rarely a lady carries a pair of cotton socks in her purse.
  5. Puerto Rican ladies use umbrellas for both a rainy and sunny day.  Yes, on sunny days the umbrella acts as a sun block.
  6. Wear proper shoes for stair climbing, walking on steep grades and uneven pavement.
  7. Wear lightweight and light-colored cotton clothes to avoid heat exhaustion.

Shopping is one of Puerto Ricans favorite pastimes.  Wednesdays are "Sales Days" at shopping mall stores. If you get a chance, consider buying from successful Puerto Rican fashion designers, they are Nono Maldonado, Mirta Rubio, Eddie Guerrero, David Antonio, Héctor Javier, Luis Antonio, Rubén Dario, Sonia Rivera, Stella Nolasco, Heriberto Vázquez.

One way to experience the fashion culture of Puerto Rico is by wearing locally - designed jewelry. Show off your hand made jewelry at the Rum Capital of the World in a restaurant where the locals enjoy good food in a safe and festive atmosphere.

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