With the notable exception of prep school uniforms for the under-10 set and AC/DC’s Angus Young (whose trademark onstage look is modeled after a prep school uniform), I don’t think the “shorts-plus-business-attire” look works:
Pairing shorts with business attire is bad enough — especially in the case of the guy on the left, who looks like he had the pants from his suit tailored into shorts — but the “dress shoes minus socks” look takes these outfits into a new realm of horrible.
Perhaps these fashionistas dream of a future like the one shown in the first season of Star Trek: The Next Generation, where some crew members of either sex wore “skants” — a cross between a skirt and pants — a subtle note by the series’ creators that gender equality had been achieved in the 24th century:
There’s a reason that even in the hottest countries in the world, long pants are the only acceptable business attire. Shorts are fine, but they work best with shirts and shoes that match them.
For more on these business attire shorts, see the International Herald-Tribune article Shorts Crack the Code.