Preppy and sexy—now all you need is a yacht.To buy: Top, $20 (available in a halter style only); bottom, $15, ae.com.
Beachy with a tank top; classic with a button-down.To buy: $59.50, jcrew.com
Great for sipping caipirinhas or catching fireflies.To buy: $88, vineyardvines.com.
An easy companion for those upcoming weddings.To buy: $198, stevenalan.com.
The warm-weather version of tailored pinstripes.To buy: $69 (available June 1), jny.com.
A wedge heel and ankle ties lend a little sass.To buy: $90, sperrytopsider.com.