Yes.  Sockless.  Do it.  I'm a fan when it's a casual look.  I'm not a fan, however, of the currently trendy look whereby one wears a suit or a jacket and tie with high water pants sans socks, ESPECIALLY when worn with leather lace shoes or monk straps.  Don't do it!

I agree,  maybe we're being a little hypocritical,  I did the above when I went to a 30th Anniversary party, well I went with socks,  it might of been the 4th whisky and coke or the 5th glass of champagne that made me loose the socks... in seriousness,  the current mood in menswear should be helping aid our look since the words ivy league style get thrown around a lot,  the problem is it's by people who don't understand it like us?

Yeah, I just hate this look. It really emphasises the loafers already very feminine style so that basically it ends up looking like a bloke body with lady-feet..hairy lady-feet. Really unattractive, male ankles are not things of any great beauty.
There was a pic of Chensvold from a while back wearing white jeans and loafers with no socks. Camp as all fuck!

I am with Woof on that. I am sans socks at the moment, wearing lightweight trousers, a linen BD, seersucker jacket and driving mocs... In loafers I mostly use socks, sockless is driving mocs, boat shoes, canvas sneakers, mostly with shorts or high water casual pants.... Rivieras are also worn sans socks, but almost ever with shorts...

I'm sockless more often than not this time of year, but only in the right kind of shoe. Unlined loafers, moccasins, and boat shoes. If I had canvas sneakers, I'd wear them sockless. If my bucks were unlined, I'd wear them without socks too. Works best in a worn-in casual shoe.

To be honest, my daily uniform consists of boat shoes (with which socks are a faux pas) worn with jacket and tie (never a suit). I strive for a relatively casual look (eg, Keydge + knit tie) but require myself to wear a tie for class. It looks better with pennies, but mine only work with socks. And in this weather, once you go sockless, it's hard to convince yourself to return to the stuffiness of socks.

If I had better unlined loafers, I'd certainly wear them more often than my boat shoes. As a matter of fact, I'm expecting a pair of Rancourt Venetian mocs to come in the mail rather soon. Hoping they pull my look together better than topsiders.

Sockless - no. Don't like it. Sorry guys but a nice pair of very light beige cotton socks is way cooler. Maybe if you're under the age of 21 it's a different matter, but I'm not.

It's certainly not a black and white issue with me. There are plenty of times where going sockless is perfectly acceptable. The real trick is knowing when and where. I feel as though most of the forum members know when they can get away with it.

hahahahaha!