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Vacationing in the Caribbean is on most people’s bucket list. The sun-drenched atmosphere, year-round warm temperatures, and dreamy beaches make the region a top travel destination. Luckily, I never had to yearn to vacation there—I grew up there. San Juan, Puerto Rico, is one of my two hometowns (the other is Caguas, a central town south of San Juan), a reality that seems like it’s from another life (I’ve lived in the New York City area for nearly a decade now). Yet, what stays with me after all these years are the memories of the most stylish people I know: Puerto Ricans.
The archipelago is beaming with sartorial prowess. Looking good (or, “de punta en blanco”) is an ethos that’s embedded in Puerto Ricans from a young age, resulting in a constant display of ruffled dresses, gold hoop earrings, and chic espadrilles that are easy to spot on a visit there. So I wasn’t surprised when New York-based designer Frederick Anderson decided to stage his latest fashion show in San Juan and jumped at the opportunity to see his Puerto Rico–inspired lineup in my hometown, as well as spend a fashionable holiday with my family. I also took the opportunity to visit and shop from some of the most exciting local designers and brands elevating Puerto Rican folklore, as well as boutiques building the archipelago’s vintage market.
Ahead, everything I packed, wore, shopped, and saw during my stay in San Juan.
What I Packed
While I grew up in Puerto Rico, that doesn’t mean I know how to dress for its weather. During college, I notoriously wore black leather jackets on 90-degree days because it made me feel more stylish than a climate-appropriate tank top. But my frontal lobe hadn’t developed at that point. For this trip, I was excited to flex my sartorial muscles with items that sum up the perfect outfit formulas for both my style and the weather forecast.
I focused on packing versatile and breathable items, making space for separates to mix and match with, instead of dresses or one-pieces. A must-pack for me is a handwoven white tank top (pictured below) made by my grandmother, Georgina. It’s delicate and incredibly cool (literally and figuratively), and a craft that’s found in many local markets in Puerto Rico. Other highlights in my suitcase include a white ribbed tank top from Arket, a black tank top from White House Black Market, and a gray asymmetrical structured top from Aritzia.
For bottoms, I needed a mix of casual and dressed-up options, given I would be going to coffee meetups and running errands, as well as attending a dinner at the beautiful Vanderbilt Hotel and a fashion show at the Antiguo Casino de Puerto Rico, both of which are at the top of my must-visit list. So that meant: a set of black wide-leg trousers from Everlane, a pair of knee-length denim shorts from Arket, my go-to black wool shorts from Banana Republic, and a pull-on pair of leopard print shorts from Damson Madder. For shoes, I packed a pair of sneakers, two pairs of kitten heels, a pair of black cowboy boots (those are more for countryside outings, trust me), and a pair of glitter platforms. I still needed shoes that were more practical, which is why I ended up borrowing a pair of my mom’s jelly sandals from Melissa. It pays to have a stylish mom.
What I Wore
While I wore over 20 outfits during my three-week stay, here are some of the highlights, and outfit formulas I genuinely recommend wearing when visiting Puerto Rico.
For a Beachside Dinner
Frederick Anderson’s team hosted a marvelous dinner at 1919 Restaurant—known for its gourmet take on Puerto Rican cuisine by Michelin Star-rated executive chef Juan José Cuevas—inside the iconic Vanderbilt Hotel. Since there was no dress code announced, I went with an off-duty look that was still work-appropriate (it was a professional dinner, after all). My Aritzia asymmetrical top and Everlane trousers were ideal to pair with the most comfortable heels I own—the Frankie4 Footwear Coco slingbacks—and a classic black mini bag from Gucci.
For a Shopping Day
It’s no secret that Puerto Rico’s weather is hot and humid—even in the winter months. So, when I decided to spend the day shopping at the popular Calle Cerra in the Miramar neighborhood, which is booming with new boutiques, restaurants, and coffee shops, I knew my outfit needed to be heat- and sweat-proof. A tried-and-true formula: a white tank top with a thin cotton button-down over it, paired with breezy shorts and sneakers. And that’s exactly what I wore: my white Arket tank top and a striped button-down shirt from AG Jeans with the leopard print Damson Madder shorts and Puma Palermo sneakers. One way to make an otherwise basic outfit more interesting is to go for clashing patterns, like the vertical stripes and leopard print I wore. Even if you’re a neutral dresser, like I am, choosing prints in muted tones, like white, black, and brown, is a foolproof way of venturing just a touch out of your comfort zone.
For a Day Trip
What most travel guides don’t tell you is that some of Puerto Rico’s best-kept sights, beaches, and experiences are not in San Juan. One destination that’s worth the one-hour drive is the Castillo Serrallés in Ponce, a town in the south of the main island, which was the home of the family that birthed Don Q rum. When my family decided to make a day trip there, I knew I had to dress the part of a wannabe Caribbean heiress. A linen halter top by Puerto Rican designer Yayi by Yayi Perez and white maxi skirt from Cuyana suited me perfectly since Ponce is one of the hottest towns in Puerto Rico. Of course, I brought along the best accessory—a hand fan.
For a Fashion Show (Or a Fancy Outing)
It’s been more than a decade since I last attended a fashion show in Puerto Rico, where I started my career. Needless to say, I wanted to show off for the Frederick Anderson fashion show, which was inspired by Puerto Rican heritage and full of nods to the archipelago’s landscape and cultural richness. I chose a Frederick Anderson red satin blazer, paired with Banana Republic wool shorts and Nordstrom white mules (sadly, they’re sold out, but these from Reformation will do just fine).
For a Trip to the Countryside
Puerto Rico’s coastal towns are super hot, but the countryside is a different story. In the winter months, temps can drop to the mid-60s at night. So, I needed a look that could withstand the daytime heat and the nighttime breeze. Western fashion is actually pretty popular in the countryside of Puerto Rico. That’s why I opted for a black denim shirt from Levi’s and matching shorts, paired with black cowboy boots.
What I Shopped
Puerto Rico’s fashion scene is small but mighty. And a collective of young designers is making sure it grows in more innovative, sustainable, and locally-rooted ways. Amid a decades-long financial crisis and rampant gentrification, many Puerto Rican designers are refusing to leave the archipelago and, instead, betting on their home turf to make their fashion dreams happen. It makes shopping there all the more special.
One of my first stops was Yayi by the designer Yayi Pérez, who opened her brick-and-mortar pop-up store on the Calle Cerra. Pérez’s POV remixes traditional Caribbean silhouettes and textiles for the 21st century with a sensibility and impeccable construction that speaks to her years of training at the Fashion Institute of Technology in New York City. In her shop, you’ll find her women’s line, as well as her dedicated collection of modern-day guayaberas, a classic Caribbean linen shirt that’s mostly associated with men of older generations. But right in line with Pérez’s design approach, she’s updating the piece for a younger crowd. I’ve known Pérez since high school, admittedly, and seeing her vision come to life in person for the first time was a delight. I had to shop for something for myself: a gray linen halter top that’s perfect for a heat-proof outfit. The designer also hosts other pop-ups from local brands inside her shop. So, while I was there, I was also able to check out Isleñas, one of Puerto Rico’s few locally-made shoe brands, specializing in espadrille-style flats.
I also stopped by a vintage pop-up further down Calle Cerra, where local secondhand shops were showcasing some of their latest offerings. The resale market is gathering steam in Puerto Rico, with shops like Pitipuá Vintage, Rosario 1939, and El Baúl de Lola positioning themselves as an affordable and more sustainable alternative to fast fashion. Their wares are impressive: I tried on a 1950s chocolate brown silk taffeta dress from Rosario 1939 that was available for $30 (in New York, it would’ve been close to $200, I bet). Sadly, it didn’t fit and I had to bury it with the rest of all the fashion regrets that still haunt me.
What I Saw
The Puerto Rico I left nine years ago is worlds apart from the one I visited this December. Power outages are now as common as trips to the beach and efforts to bring in foreign newcomers (largely via tax incentives) have displaced and transformed many of the communities I loved and belonged to. But visiting local businesses gave me a lot of hope for the future of my homeland.
Take Pérez, for example, who exchanged a promising career as a designer in New York City to move back home and open her own brand, at which she employs a small staff of patternmakers, seamstresses, and retail associates. Her story is a stellar example of how betting on local talent and consumers can make a difference in an archipelago plagued by displacement. It’s also a show of how going back to one’s roots, whether designing guayaberas or making folkloric music like Bad Bunny’s Debí Tirar Más Fotos, can differentiate oneself from the cultural flattening of our time.
But what hasn’t changed is the amalgamation of sartorial characters witnessed on the streets. From the elder ladies dressed in clip-on earrings and espadrilles just to go grocery shopping to the young students wearing jewelry from local artisans to reclaim their cultural pride, I'm in awe at the sartorial richness of Puerto Rico, and can’t wait to dress up there again.