Dear Fashion Kitty, How Do I Wear Tailored Shorts?

Any clues on what I could wear with tailored shorts? Just bought a few pairs and I’m clueless because my usual leather jacket looks wrong!

Um, yes .. a leather jacket was definitely the wrong choice. A little too harsh for tailored shorts. For longer tailored shorts; I like the idea of wearing them with a simple tank and an opened button down top. For shorter tailored shorts; a tee shirt and a nice looking cardigan usually does the trick. And with any pair of shorts, wear them with flats. Shorts and heels can look kinda skanky, which isn’t always a bad thing (haha) but typically that look is frowned upon.