You shouldn't unless you own a Kentucky Derby winning racehorse, or a fleet of gondolas in Venice.
Or alternatively, you should be lean, broad-shouldered, and handsome as fuck. If you do not meet these requirements, you might look like a big ol' hard-on.
Yeah but for college age guys it's not really for many occasions that a post-grad would experience. Speaking as someone who does this occasionally, it's for crawfish boils, gameday, etc. where we like to get dress up but also are kind of just dicking around.
Yes, that's right. Dressy casual. Don't mean to suggest it's CBD.
We used to do this in college back in the day. It was upstate NY, so as soon as it got above 40 (F) everybody put on shorts. It seems to be coming into vogue now with certain designers like Michael Bastian.
Traditionally, schoolboys wore their school jacket with shorts because their lifestyle did not treat trouser knees too well. When they grew up they got to (proudly) wear real, long trousers.
This is why the combination exists at all and the "if it's hot enouigh for shorts"-comment above definitely applies.