As one of the most LGBTQ-friendly islands in the Caribbean, Puerto Rico has an inclusivity that extends well into its retail and shopping scene.

Since Hurricane Maria, the San Juan shopping landscape has been rebuilt and refreshed with businesses devoted to preserving Puerto Rican tradition and supporting global causes like female entrepreneurship. As a visitor, your positive impact is greater when you shop local brands. Here are a few locally owned places to check out while exploring the capital’s colorful, gay-friendly neighborhoods’ spectrum of shops – from artisanal trinkets to luxury fashion.

Old San Juan

Stroll the pastel-colored streets of Old San Juan to find hidden gems. 


105 Fortaleza Street

As one of the most iconic shops on the island, Olé has been hand-fitting Panama hats in Old San Juan since 1977. Plus, your ability to customize elements on the hat mean they’re each one of a kind. Olé exclusively sells hats from traditional Latin American manufacturers who’ve been in the business for generations.

Con Calma

207 San Francisco Street

Owner and designer Matilsha Marxuach created Con Calma to serve as more than just a shop, but a hub for creativity in the heart of Old San Juan. The store is best known for its original collection of bags and totes, designed by Matilsha and produced by an industrial women-owned cooperative in Utuado. You’ll also see unisex fashion from other local designers with the shared characteristic of raising awareness of fair-trade, sustainable style.

Santurce Pop, a pop-up market

San Patricio Pop, a pop-up market featuring independent local artists and merchants.


An unpretentious neighborhood buzzing with local eateries and cultural attractions, Santurce has evolved into a popular area to visit.

Santurce POP

1116 Avenida Ponce de León

Santurce POP is located about a block away from San Juan’s Museum of Contemporary Art. Swing by this sprawling warehouse space after a morning at the museum, where you’ll discover a small business incubator with a focus on retail merchants and artists. Get your glam on at EDIT Hair Salon, then peruse the different pop-ups, like the gay-owned Librería La Esquinita bookstore.

La Tigre Uomo  

Ciudadela 1511 Ponce de Leon Ave

At mens’ boutique La Tigre Uomo, founder Mario Alberghini and creative director Joseph Padró have curated a roster of exquisite Italian brands. Create an entire outfit with L.B.M. 1911 jackets, Mazzarelli shirts, and PT Pantaloni Torino trousers.

Calle Loíza

This unmissable district is an emerging epicenter for vibrant street art, culinary adventures, and eccentric shopping.

Sixne Concept Store

1752 Calle Loíza

A haven for stylish guys on buzzing Calle Loíza, Sixne Concept store is a small menswear shop founded by Humberto Vázquez. It’s the first authorized vendor of trendy Sixne streetwear in Puerto Rico, but the shop also carries other urban brands with accessories like hats, skateboards, and beach items. 

T Playa

1804 Calle Loíza

Get transported to the tropical islands of Southeast Asia at T Playa, a boutique that sells a variety of funky accessories from places like Bali that are easy to fall in love with. The boutique is most popular for its collection of intricate straw hats, bags, and hand-strung hammocks.

Libros Libres

1404 Avenida Ponce de León

A “take a book, leave a book” community project that’s not exactly a shop, but a portal to information exchange sharing of worlds. If you’ve wrapped up any of your beach reads while in Puerto Rico, drop it off at Libros Libres, where it may end up in the hands of a curious passerby.


This tony district is home to many high-end retail shops, namely on Ashford Avenue, Puerto Rico’s shorefront answer to Fifth Avenue.


1126 Ashford Ave.

Monsieur is an iconic men’s boutique in the heart of Condado’s fashion district that has introduced many of the finest fashion brands to the Puerto Rico market. While the inventory skews a bit conservative, it’s a fantastic place for shirts with vibrant tropical prints or simple guayabera, the Latin man’s quintessential summer shirt. With expert tailoring services, anything you purchase at Monsieur is guaranteed to fit perfectly.

Nono Maldonado

1112 Ashford Ave.

Nono Maldonado is among Puerto Rico’s most renowned fashion designers, and while Maldonado’s signature items are men’s linen shirts and guayaberas, he has also expanded into womenswear and even interiors, having just designed the newly-opened St. Regis Bahia Beach Resort.


58 Taft Street

At Luca’s breezy new boutique in Condado, independent designers are in the spotlight. You’ll discover one-of-a-kind jewelry pieces, home goods, and sustainable (mostly women’s) apparel from local and international names. Owner Laura Lugo-Caro designs the store’s eponymous jewelry and fashion label, which could be described as minimalist chic.

Mall of San Juan

Seeking more high-end fashion? Zip over to the Mall of San Juan for an impressive selection of fashion brands under one glamorous roof. 

Luis Antonio

1000 Mall of San Juan Blvd.

Puerto Rican designer Luis Antonio is a household name among women for his flamboyant, yet refined pieces recognized by ruffles, bright colors and seductive evening wear. In recent years, Luis Antonio has been designing a menswear line that’s understated and contemporary, worn in the past by Puerto Rican celebrities like Luis Fonsi and Marc Anthony.