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Everything you've read about Key West being laid-back and relaxed is absolutely true. There is no need for suits, ties, dress shoes or practically anything that might need heavy ironing. Think "summertime" or "Bar-B-Que at your neighbor's house" for a clothing guide.
For the months of December through March, the daytime temps will be in the mid to high 70’s with occasional evening dips into the 60’s or a daytime spike in the low 80’s. Very occasional showers should also be anticipated. Very few bugs are out and about during this time. Mosquitoes are not an issue.
For May through November, daytime temps can average in the mid 90’s with high humidity and often an afternoon downpour. The bothersome bugs make a come-back.
Honestly… No one cares what you’re wearing here. If you have to choose, here’s the best rule of thumb: Always choose comfort over appearance.
Not to be forgotten:
It's also been recommended... A foldable, cloth tote - useful for carrying your gear for a snorkling trip (even though they tell you to just bring "a towel, your camera, and yourself") You can also use it while shopping for souveniers and to carry them home. Maybe a daypack or fanny pack - to free your hands up to hold a cool drink, and to stash your book, bugspray, sunscreen or other small necessities. Drawstring sports bags work well for this purpose (just about the right size for anything you may need), but they may chafe on sunburned shoulders.