Even though espadrilles are technically a casual, seaside shoe, their simple design and profile, along with a roped sole versus rubber, can actually give an outfit a more dressed up appearance; versus say, a pair of vans, but certainly less so than the effect loafers would have. This along with some other strengths, makes espadrilles a smart choice when you have to move in and out of different kinds of events in the day.
Gap refers to these shorts as “hiking shorts” but that's just a way to call out that the front pockets have visible seems. This is a simple way of giving a pair of flat front shorts more visual interest, a tool you can make use of if you think your outfit is missing something or feels too simple.
The floral pattern, as well as the modern fit, on this short sleeve oxford shirt keeps it from looking like a uniform for a big box store. And the extra structure provided by the oxford cloth allows you to transition into less casual venues as the day goes on.
The fit on this shirt is near perfect. You want the tail to hit about midway down the fly on your shorts, and the sleeves should be slim to the arms and end right around halfway down your bicep, though depending on the shirt they can be a smidge longer.