I think that the intresting question is whether shorts can be made acceptable in this menswear section. It seems a little silly to me that shorts are considered a faux pas whereas wearing slacks and dress shoes without socks is fashionable. Ivy league campus pictures from the 50's and 60''s show lots of examples of men wearing shorts (my standard for preppy), often with loafers . Shorts are worn in summer actives, are the standard wear for backpacking/hiking. I think they represent more of a spring/summer option than hot weather option. They may not have their place in the office environment, or the more dressed up environment, but SF does have a decent amount of discussion of acceptable casual wear. Skinny, underdeveloped legs aren't going to look good, and should not be exposed out of politeness to others (just like some girls can expose their midriff and other should definitely not) but muscular well developed legs with no signs of aging certainly look fine.