
After observing thousand of visitors and locals tread past my door trying to keep cool and look chic at the same time, I am qualified to offer a few summer fashion pointers.
Undergarments: It should not be obvious to a passerby that you either are or are not wearing a bra.
Capris: Wear them if you must, but know they are doing nothing for you. If you are going to the trouble of putting on pants, then wear real ones, which will make you look taller and thinner, and who doesn't need that? If it's too hot for pants and you can't face the exposure that shorts offer, then opt for a summer dress. They are cooler than capris and look better.

Summer dresses: A great way to stay cool and still look civilized. Note that two percent of the world's population looks good strapless. Also, if the dress hangs only inches below your bottom, it is not a dress; it is a swimsuit coverup.
Flip-flops: Great for the shower or poolside schlepping. Not to be worn in public otherwise.
Boots: Boots are stylish. Boots are hip. But if it's 95 degrees out, boots are nasty.

Any tips you'd add?
Images: Style Sightings via Definitely Golden; Hayden+Harnett via The City Sage; J.Crew summer catalogue.