Von Franz said:"It's fine, just so long as you can pull it off with confidence.
Your shorts and loafers have to be objectively stylish, too.
People forget to apply regular standards to shorts sometimes, and it's a shame.
Don't wear douchey shorts, or douchey loafers.
If you wear either, you'll look like a douche.
If you wear shorts that fit well and are relatively subdued, and loafers you'd wear with normal pants, you have a fairly good chance of making it work.
No socks.
None."
I think you nailed the main reason why this style has a bad reputation. Many boys have ill fitted shorts and shirts baggy and even tucked, some loafers also complete the "yacht club" or Miami Vice look :)
This is why I think, well fitting shorts and shirts untucked, maybe with a touch of modern/sporty is well advised. Loafers also look better to me if they are plain and "casual", I mean not decorated. The whole look have to be carried off to not look pretentious.
As I said, I prefer the sockless look, even as a feeling, it is comfortable especially if the loafers fit like a glove. I simply don't think socks don't look so bad, I'm obviously talking about those socks that don't cover too much and stop barely at the ankle. There can be style on the socks too, you can even go creative with the colors, but yellow, orange, and white, and any bright shade which would look too much over the top, so darker shades of greenish, bordeaux, burgundy purple, gray or striped can be easily paired even if you gotta pay attention they don't fight with the rest of your outfit colors.
Anything looking ok with converse or other shoes can also look ok with these loafers, as they are not dressy, the purpose is rather a playful yet stylish look.
It obviously can't be for all tastes, if so you can avoid the socks.
I revalued the socks when I saw some girls rocking them with heels and skirts, which I once thought it couldn't ever look good. Now I think they can be stylish and one can flaunt them.
Bye
