untuck for you, not for me

I see you guy with the tightly tucked in shirt. You had your launderer starch that thing didn't ya? You didn't go for starch because it feels great to wear that way but because someone might judge you down at the office if you came in with a wrinkle. I've got news for you. The only person who will judge you are the other starched, tucked in shirt guys and ladies. No one else cares. The comfortable shirt guys are not wondering what anyone thinks. That's why they can get away with wearing the comfortable shirt. Look, I've tried hanging with you both and I have to say, the comfortable non-tucked guy knows how to be happy. You can wear a comfy shirt. Hey, it might even save your life.

I love this scene from the Break-up and it's a perfect illustration of the two shirt guys:

Gary Grobowski: You want to go get a drink? No.
Brooke Meyers: I'm with somebody, sorry.
Gary Grobowski: Who? The guy with the tucked-in shirt and the visor? What, is that like a brother? The guy was not your brother, then.
Brooke Meyers: He's not my brother.
Gary Grobowski: Who is this guy? Who's this... I'm getting mad now. I'm jealous. Who is this guy?
Brooke Meyers: Who are you?
Gary Grobowski: I don't know. I'm kidding with you. Who's the guy with the tucked-in stuff? Is that a boyfriend?
Brooke Meyers: It's...I'm going.
Gary Grobowski: Do you think you'll marry him? Cause I know you've thought about it. The first time you laid eyes on him, you probably thought, I wonder if I could marry this guy in plaid shorts who tucks his shirt in. Then when you kissed him, you said, I can't believe it. I had a lot to drink tonight. I'm kissing the tucked-in guy. My point is, if you're not gonna marry him...and if it's not forever, then you really don't have anything to lose in taking me up on my offer.
Brooke Meyers: Well, I'm gonna go.
Gary Grobowski: Okay. Me, too. To where? On an ice-breaking first date?