For my Puerto Rico look, I threw out any seasonal logic, because there are no seasons on the island.

Staying true to my personal style, I pulled a blazer, but one that's super light and casual and just colorful enough to complement the rich colors of the plaster walls of Old San Juan. I kept the color palette pretty contained with a lavender shirt and tan linen trousers and topped of my look with a Panama hat that borders just on the right side of cliché (in my opinion).


Jacket: Eleventy | Shirt: Canali | Pants: Banana Republic | Hat: J.Crew | Shoes: Zara (similar here) | Sunglasses: RayBan | Watch: Shinola | Pocket Square: Madewell