the 90s skater shoe

Look, you know what I'm talking about. The puffy tongue, thick soles, falling off your feet, usually accompanied by too-baggy jeans and a love of Wu-Tang Clan. 

What the shoe indicates:

He's back partying like it's 1999, and maybe hanging out with middle schoolers (yikes!). But hopefully, he lives in Dogtown, because otherwise, there's no excuse for wearing these uglies. Besides, nobody wants to share the same shoes as Taking-Back-Sunday-listening, preteen girls. 

Maybe you could ask him to clarify how wearing shoes that are way too big for him help him  grip a board better. 

Let's show him some updates, shall we?

That is soooo much better.

Dating guide:
The 90s skater shoe wearer is old school. And probably cheap. That doesn't mean he's not likeable, but it does mean he needs an update. And probably a more recent shower than, say, every three days. The good news is, he has the appeal of mystery, and who doesn't love that? (Will Scooby-Doo ever find out where his last pair of clean boxers went? Stay tuned...)


the top-sider

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.

Dating guide:
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.