If you went down to any beach here in England duing the summer you would understand the meaning of "naked with socks". You will always find a batch of middle aged men wearing socks with sandels and shorts on, this creates a geek culture around people wering socks when you shouldn't, ie when naked.
The best way to find out if you can pull it off is to stand infront of a full length mirror with you socks on and otherwise naked, and see how silly you look. This would be a turn off to a British woman, hense the reference "naked with socks"
I think ???
Cheers
Cris.