Gregory is in my top 10. I love it, and I'd be thrilled to see it on a little boy. It does have a sort of mid-century feel, but it hung on to the top 100 through most of the 90s, so I don't think it's tragically outdated. I lump it with names like
Richard,
Stephen, and
Philip: a classic, manly name currently experiencing a downturn in popularity.
If anything about
Gregory is clunky and outdated, it's probably
Greg. Luckily,
Gregory has other nn options. I like
Greer,
Gregor, and
Rory.