So I go to my handy dandy art of manliness to address this issue.
So, how short should your shorts be? Short enough that your knees are visible or just slightly covered if standing still. Long enough that you’re not showing the world you rarely tan your thighs; if I have to be specific, I would go more than 2-3 inches above the knee, depending on your proportions. Barron from the Effortless Gent backs me up here.
Anything past the knees has ceased to be “shorts.” Those are high-cut pants, which is something else entirely (and not very flattering).
Shorts that do come up to mid-thigh should be limited to lightweight athletic shorts, and should only be worn in athletic settings. Running shorts get more leeway than casual shorts because the expectation is that you’re not going to walk into a store or restaurant wearing them. Exercise devotees should bear this in mind, and should go home and change (and shower) before inflicting themselves on the public outside of gyms, courts, or bike paths.
So, yes, I've seen all three lengths here in Jamaica, and even some lengths that, me being a man, will not dare to display... EVER!!!! I've worn shorts above my knee all weekend, but there's a limit to it all. So, reaching back to our first post, I don't knock anyone for it if they say it's their style to wear speedos or briefs and call them shorts... Before this post... But when you know better, you do better, so here is an outline for you to correct your mistakes. Don't be that guy.