Answer 1 Well, I'd say it all depends on the colors, socks, etc. In some cases, it is, but I'd be very careful, as it can easily go wrong.
Answer 2
It's perfectly okay, they are socks and we all wear them. If you are uncertain about type and color and don't wan't to stand out, black light ankle socks with black flats and a nice skirt are always sexy in classic way, so you can't go wrong, it's almost like not wearing any socks.
Though, if you wanna unleash your fantasy more and let it go, don't be afraid of standing out with nice color socks, if you know how to match. It can be wise to match socks with tops.
Grey is also very nice for an everyday look.
Azure grey sock worn by Alexa Chung with a more creative yet classic outfit
(yes, if Alexa's legs were more shapely she would pull it off better, but most girls aren't this skinny, even if, I dunno why many would want to).
Azure socks with brown "boho" or turquoise tops.
This one can match a plaid shirt (related links).
A little more on the daring side you can wear the long socks above your knee.
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