Are these shots artistic or unskilled? I'm not sure. Anyway, it's an outfit. Sometimes it's fun to mix up your expectations for casual shorts with a blazer and dressier top. Obviously the reality of these types of outfits is that you can only wear them for specific temperatures, but perhaps one cool summer night, you may have the chance to slip away for an evening concert or outdoor play. If so, I offer my humble idea for a possible outfit.... Have fun!
Blazer: thrifted (similar)
Top: Marshalls, long ago (similar)
Shorts: Old Navy (exact)
Shoes, Via Spiga via ebay (similar)
Bag: Vintage Coach via ebay (similar)
Earrings: Spain vacation, long ago (similar)
Hat: Charlotte Russe (similar)