This is an outfit I would wear any time. It is going to allow you to be comfortable in almost any situation and can go from androgynous to Tom Boy based on your shoe choice. I have really come to appreciate the Tory Burch line for its feminine fit and style. Thanks Bri . You could always pair this with your Keds and make it work in almost any circumstance (guy/gal).
The Brooks Brothers bag is practical and can carry almost everything you would need for a day/week. Even if the day was a stop by the beach. This Brooks Brothers "Calfskin Bucket Bag" is on sale for an amazing 70% off.
The denim shirt is available almost everywhere. I show it above in the J. Crew version however, both Banana Republic and Talbotts has it. Make sure the material is light so it hangs. I have found this to be an item that travels well and is great for a casual evening.
I love my white denim jeans. They go with so much and I have then in a Jag pull up style (flat front) and in the above boot cut from Talbots. This is my true wardrobe staple.
My Tiffany sunglasses are from my favorite eyewear shop Eyes On The Island in Palm Beach. Ben is amazing to deal with and provides great prices, whether it prescription or not. They have many styles from casual to elegant.
Shop or pick an outfit you already have; mix and match. But most important - "ESCAPE".