The first one also has a hood. I really like it, but not sure if it's the right choice or not.

The second one's stripes actually are a perfect match to the shirt. This is also a nice flannel, but not sure if the color scheme is too dark or not.

I'm gonna be wearing these with some light jeans, and some white & blue Jordans.

I'm trying to ask a girl out tomorrow, and wanna look my best.

I should add that the shirt is a nice American Eagle shirt with a lighter shaded eagle in the front