backwards
baseball hat

Do you play catcher for a major league ball club? Minor league? Local softball team? No? Then don't do this.

oakley blades

Your Tour de France riding days are over, pal.

bluetooth headset

1. Trust us, you're not that important.
2. You're now just one-degree removed from Lando Calrissian's bald android assistant.

gold necklace

Rap moguls, NBA stars, and Mr. T excluded. Some white guy from the 'burbs, nuh uh.

tommy bahama shirt

When in Hawaii, this is OK. In the upper 49, toolbag.

national review magazine

In close association with bad style, bad politics.

belt-clipped cell phone

Scream "I am a middle manager!" a little louder. The guy across the street didn't hear you.

"cause" wristband

Exceptions made if you or immediate family member is battling various wristband maladies. Otherwise, grab a scissors.

over-the-knee, double-pleated shorts

Two things wrong here:
1. 4 pleats.
2. Over the knee.

crocs

Here's a good rule to live by: Never wear the same shoes as your 5-year-old nephew.