I like that this look says "Yeah, this is the most relaxed I get. Sure, I'm wearing a tie and wingtips, but the pants are casual-ish, right? And the pullover is maybe something you'd wear on laundry day? Eh, screw you - it's me."

I like this look so much, I'd even style my hair to match.

It's like, "How can we make Mr. Rogers even more juvenile?" I should hate this, but I like it.

I hated this look when I first saw it but am now warming up to it. The top half but had issues with how it relates to the bottom half.

Nerds, glasses, tone-on-tone shirt/tie, somewhat inappropriate shoes (black would have been better, no?)... and a not-so-tiny dog as an accessory.