Now, the Sperry Top-sider has been called a sailor shoe. But I really don't know any sailors that would wear this shoe unless posing for an L.L. Bean or Nautica catalog shoot. And we all know models can't sail.
What the top-sider indicates:
You're preppy, value comfort, and like the feel of shoes without socks. You probably also own Rainbows. Most of your outfits match your Sperrys.
OR, if you fall into the category of a boy with side-swept hair pairing Sperrys with skinny jeans... though casual, you're probably better dressed than most girls in any given room. You often feel it is appropriate to wear Sperrys with uncomfortably-small J.Crew shorts. Hmm.
Sperry wearers are mostly low-maintenance and are often mama's boys. But, due to being mama's boys, on the first couple dates, they'll probably be be courteous and open most doors for you.