New York...New fashion statement?

I was doing my daily reading on Mediatakout.com, and they shared a picture of what the homies out in New York are rockin...

I have the following questions:

1. What the heck does a dude put in a carry on bag to walk down the street?

2. The dude on the left definitly has the biggest and fullest bag, where is he going?

3. Why is the guy on the left smiling so hard?

4. How did he make that cut?

5. Where did they get those smedium sweatshirts from?

6. Is that another trend?

7. Can they give that back to whoever they got it from?

8. wait...is that Madonna on the red sweatshirt?

9. Wouldn't those bags get heavier as the day passed?

10. I guess dude on the right can use his shoulder strap.

I don't know if I'm too into this one. Imagine being out with a dude and he has one...he fly...but he wears a carry on daily.

Ya'll go out somewhere and he says: "Baby, can you hold my purse while I go to the bathroom?"