Or if your name is secret & everybody calls you The Doctor!
I guess I should have better differentiated between “not at all ok” and “something I really dislike”. It just seems like “geeky teenager who wants to dress up but only owns black oxfords for church” more than “Boston Dot-com Happy Hour” to me. But I accept your interpretation and agree it’s no where near as “wrong” as mismatching your shoes and belt. It’s strong personal preference that leads me to dislike it.
This is so critically important that it needs to be elaborated upon.
All the money in the world will not help you if you don’t buy clothes that fit properly. Ill-fitting clothes make you look like a hobo. A $1200 suit that isn’t the right size just makes you look like a hobo who had the foresight to root in a dumpster behind a Hugo Boss.
While “Get clothes that fit” this may sound rock-stupid, a truly amazing number of people do not wear properly fitted clothes - they have shirts that wear too loose, or sleeves too short, or pants too long or too short or too wide in the seat, or any number of problems. The difference in appearance is VERY significant.
The junk off the rack at Target and Wal-Mart might fit you, or it might not; the gamut of fits is limited. (None of it works for me because the length is never right; apparently 6’2" guys can’t shop at Wal Mart. I either end up with a shirt that fits my shoulders and chest but doesn’t go down far enough, or one long enough but is big enough to make me a contender for the America’s Cup.) The advantage to going to a real men’s clothing store, even if it’s just a Men’s Wearhouse - which provides perfectly good clothing for all but the most snobby occasions - is that you can actually have a professional measure your clothes and ensure they fit correctly with, if need be, a few alterations.
But “dress sock” or “white sweat sock” are not the only options. I’d wear black or blue socks with that shoe, but I’d only wear that shoe with jeans or dark black or blue very casual pants. It’s too dark a shoe for khakis or light-colored pants. I say “I” because I actually own a pair of shoes much like those; they’re very comfortable but as stylish as if you tied a pair of life jackets around your feet.
To me, nothing says “geek!” like white sweat socks with dark pants and shoes. Except wearing them with sandals, of course.