The photo spread above is from the mid 1980s, the original hey day of socklessness. Here, it's pictured as a mark of nobility of sorts (click to enlarge and read the caption, it's worth a good chuckle). Now, I'm in no way trying to belie the humbleness of my blood line, but I do like a bare ankle in the Summertime. There are, however, a few guidelines I adhere to regarding the sort of shoes suitable for this little affectation: loafers, canvas sneakers and moccasins.
and of course, the classic Sperry Topsider, in dark brown with a white rubber sole. If ever a shoe wanted socks less, I haven't found it. The unchallenged classic with shorts, khakis, jeans, blazers, you name it...just not socks.
Not wearing socks should be an easy breezy affair...but it can run amock:
I don't want to get all bitchy and trash this kid. After all, he does look better than 90% of men on the street, and he's clearly taken an effort to dress well ( even if that effort mostly consisted of doing the Ralph Lauren dance...as a slow dance...). I'm willing to cut the kid plenty slack. But this recent trend of hard soled lace up dress shoes sockless? I'll forgive the tie and shorts combo, I'll forgive the looking-at-my-watch-staring-the-other-way-affected-New York-pose...but the brogues without socks thing has got to come to an end. On the other hand, as a swarthy Italian Catholic, I'm gonna go ahead and give Jewish Ralph and this handsome young black fellow a million combined points for furthering the cause of wearing these kinds of things for their own sake. The more curmudgeonly types on the webs may be loath to admit that anyone of the unwashed savages(such as myself) has any right to wear this stuff, but, like the pants and the bare ankles said...go to Hell?
p.s my apologies for the fact that the last few posts have included only reposted photos or those culled from the internet. Photo uploading and editing difficulties on my end should be resolved soon.

