Another flexible and friendly item to have in your closet is a quality pair of dark denim jeans, deep dark blue but not black. I also think they shouldn't be flapping in the back or super loose, they shouldn't be tight but they shouldn't be super loose either. 
This particular style and color denim allows you to throw so many different style shirts with it. Florida is hot and typically I do not like pants of any kind in the summer but these ones I own by Tommy Bahama are pretty thin and super comfortable, I didn't even pay much for them thru a big sale recently, again at Macy's. You can throw on a dress shirt, resort style, polo, t-shirts, grab a sport coat and dress it up if you want.
White dress shirts are also a lost art. You want something crisp and tailored. Doesn't matter what size you are, you don't want the shirt flapping everywhere, also don't want it overly tight. I prefer no button down on the collar but others swear by that look with a collegiate style tie, personally not my thing but many do it. And if you have done the dark pants/jeans, the crisp white dress shirt, now you can go for broke on the tie and try a n array of screaming colors if you need that to match your personality more.