Activity: Errands and appointments
Sweater: J. Crew Factory, old
Top: J. Crew, old (I wish you could see the detail in the photos, it's beautiful black eyelet with a ruffle at the neckline)
Shorts: Old Navy, old
Shoes: Charles David via Nordstrom Rack
Bag: Marc by Marc Jacobs
Watch: vintage Citizen via ebay
I think I've sort of figured out the "making shorts look presentable" thing (feel free to disagree). The key, for me anyway, seems to be NOT using a regular tee shirt with the shorts. Thankfully, in summer, a woven cotton top is usually 1) easy to find and 2) cooler than a knit tee. So just that simple addition seems to add a bit of spice to a simple outfit.
Although you can work with a tee and shorts, too. I go there regularly...