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Sherlock - meaning is "bright hair". My hair isn't bright, but it's a neat name. If I took that name, people might start nicknaming me "Shirley" though. And while Sherlock is neat, Shirley would be ewww for me. Calling oneself Sherlock would probably be seen as pretentious though, sort of like changing your name to Einstein.
Sherwood - meaning is "luminous wood". Doesn't sound as nice as Sherlock, but sort of cool too, in a Robin Hood way. But it sounds too much like, "Sure would!". People might start joking, "Oh yeah? You sure would what?". Actually, might be good for a last name.
Sherwind - meaning is "bright friend". Haven't come across that name before, at least not spelled like that. Variant of Sherwin / Sherwinn / Sherwen / Sherwyn, etc.
Sherwood - meaning is "luminous wood". Doesn't sound as nice as Sherlock, but sort of cool too, in a Robin Hood way. But it sounds too much like, "Sure would!". People might start joking, "Oh yeah? You sure would what?". Actually, might be good for a last name.
Sherwind - meaning is "bright friend". Haven't come across that name before, at least not spelled like that. Variant of Sherwin / Sherwinn / Sherwen / Sherwyn, etc.