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Yes, Waldo has a silly/dorky image to me. And a clunky/dusty feel as well. I grew up with "Where's Wally?" books, but I don't think they're as popular now as they were back in the '90s, so that association alone wouldn't put me off using Waldo/Wally if I was so inclined. On the other hand I find Walter sophisticated, refined, intelligent, strong and handsome.

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Arlo, Leo and Milo are "lighter" than Waldo. Not dorky, but more youthful/immature. I guess you could say they're "cool", although they're not my taste - they're better off on dogs/cats in my opinion!