If you are going to go to Key West be it for vacation, to live, or loot & pillage, it does help to dress correctly for your island stay. Nothing says tourist or mainlander like a heavy dark shirt, denim cutoffs, and socks with sandals. If you are going to be on the island, look like you belong on the island.
So here, based on my vast experience, (recent location not withstanding), and as a blatant excuse to put up some affiliate advertising courtesy of Amazon, are my recommendations for proper island wear.
Stick with light colors when making your choices. The shirts come with built in sunblock which comes in real handy. Everything is light in weight and dries very quickly. There are other options for shirts and shorts but I’ve found these to work the best. These clothes are comfortable in the heat and sun, and look good for just about any occasion from fishing to hanging out in your favorite watering hole. And you won’t stick out like a damn tourist.
And who knows what sort of mermaid or sea creature you may lure with your new wardrobe?
You are on your own for underwear, if indeed you choose to wear any.