Best: Chris Rock / Worst: David Spade
Rock is doing thick-rimmed glasses right: slim-cut suit, natty bowtie (the "natty bow" is a term we have now officially coined), and an acceptable afro.
Spade on the other hand... is losing. Awful pants, unbuttoned jacket... and just plain bad sneakers. We have no problems with rocking sneakers with a suit, but only if it's done well, meaning with tailored pants and no bunching at the bottom. Right now he looks like a rebellious skater kid who decided to dress up for prom but plans on getting really high in the bathroom.