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Leopold and Leonardo are two of my favorite names (though these days Leopold is ahead). It definitely does have a more "silly" vibe than say Leonardo, but with the nn Leo it makes it seem more usable.
As much as I love Leopold, I'm not sure if I'd be able to use it either. I think that it's absolutely the cutest name ever for a little boy, but it seems to get more "silly" sounding with age, imo. As of now I'm probably more likely to use Leonardo, even though I love Leopold even more.