What to Wear (and Not Wear) in Old San Juan
Old San Juan (and other colorful locations) is already visually loud—in the best possible way. The saturated blues, yellows, greens, and weathered textures of the city do a lot of the visual heavy lifting. Because of that, what you wear should complement the environment, not compete with it.
Avoid extremely bright, high-impact colors—especially oranges and aggressive reds. Those tones tend to overpower the frame, pull attention away from the architecture, and visually “flatten” scenes that otherwise have incredible depth and character. Color is absolutely welcome, but it should feel intentional and harmonious with the city, not louder than it.
Modern digital editing techniques and preferences also tend to lean toward more saturation and these bight colors can dominate a saturated image.
That said, there are practical considerations as well:
Black photographs beautifully—but it can be brutally hot. Between the Caribbean sun, stone streets, and reflected heat, all-black outfits often become uncomfortable quickly. If you are comfortable with heat and humidity, then don’t run away from black. If black is part of the look, consider lighter fabrics or broken-up layers.
White, linens, and soft pastels work exceptionally well. These tones echo the ocean light, feel breathable, and photograph cleanly against the colorful walls and cobblestones. They also help keep you cooler. Add small splashes of color or light patterns.
Bring a small towel or cloth. This sounds minor, but it matters. Old San Juan is warm and humid year-round, and a quick wipe between setups keeps skin looking fresh and polished.
Sunglasses can be both functional and fashionable. In especially bright scenes, they not only protect your eyes but can add a relaxed, confident edge to the images—particularly when styled intentionally rather than as an afterthought.
The key idea is simple: let the city shine. When your wardrobe supports the environment instead of fighting it, the result feels effortless, editorial, and far more timeless—exactly what you want when shooting in a place as visually rich as Old San Juan.