A cool pair of shades, a super cute swimsuit, a good pair of jean shorts, and cool sandals.
A really chic jacket to make every outfit look more put together, some cool boots, a nice sweater, and chic sweatpants.
Somewhere in Between:
A cool leather jacket, a statement bag, a good pair of jeans.
Somewhere with Walking:
If you're going to be walking a lot I suggest a mini backpack. They sell really cute ones like the one featured in my "Travel Essentials" post. I also love a cool pair of sneakers. The adidas ones are really cool and in.
Somewhere with Drizzles:
Waterproof shoes, a cool rain coat, and a pair of jeans/leggings