Whenever I think of summer style icons, the ever-classic, easy breezy Kennedys always come to mind. They always looked comfortable with just the right amount of prep in the New England sun. 
Want a modern -Jackie/Jack look? Here are my picks:
A retro shift dress:
The must-have oversized shades:
An always-classic nude heel:
Top it off with a structured, but modern bag:
How gorgeous is that Harper bag? I’m loving the tassle!
And for the Jack in your life?
A light, casual shirt:
Boat shoes, even if he’s not a sailor:
The ever-present Ray-Bans:
And a retro watch to top it off: