Tell Me What To Wear!

Guys... I am such a mess. And I need your advice on this date. I really can't decide on what I want to wear. I know this counts as obsessing, which is what I SHOULDN'T be doing right now... but I can't help it. So you guys might as well help me out.

SO, I took a bunch of pictures of myself in possible articles of clothing that I can wear to the date. PLEASE let me know what you guys think of them. (The pictures are small, but you click into them to make them bigger)

First Decision: Which pairs of jeans?!

Jeans #1: Express Men. Low Rise Straight Fit. Dark wash.

Jeans #2: Express Men. Low Rise Boot Cut. Faded wash.

I'm leaning towards Jeans #1 because they're a little tighter, but they're also kind of restricting in movement. As in, I can't really squat down too well because they're kinda tight. But when am I going to need to squat, right? Jeans #2 are definitely more comfortable. Do you guys like the faded wash in the front? They're just a bit more baggy and therefore makes my thighs look huge.

Second Decision: What top should I wear?!

Top #1: Heritage. Light Grey Graphic T. Argyle + Design. (w/ optional jacket because it'll be cold)

Top #2: Gap. Red collared shirt. Semi-tight fit.

Top #3: Heritage. Black Graphic T. Argyle + Design

Top #4: Heritage. Blue/White button-up shirt.

Ok, so I narrowed it down to these 4 options for the tops. I just kept my tight pair of Low Rise Straight Fit jeans on for these pics. I'm not sure if I'll need a jacket or some outerwear because the forecast says a high of 81 on Sunday. (Jeez! I thought it was Fall!) But I'm guessing the temperature will drop at night, so I'm thinking I should plan on wearing SOMETHING. Deciding on that is going to take more time...

Third Decision: Which pair of shoes?!

Shoes #1: Puma. Black w/ White design.

Shoes #2: Adidas. White w/ Black stripes.

These are the two pairs of shoes that I'm consider to go with the outfit. I guess it depends on what I'm wearing for my top. But the black Pumas are super comfy. The white Adidas are a little more stylish, but they kinda hurt my feet because I think they're too narrow. My left big toe pushes up against the tip of the shoe and it sorta hurts after a while.

So I need all your help! Let me know if the tops are too casual or too formal or too ugly or whatever. Just help me out! I can't decide! Or let me know if I should just buy something new. I just got a comment from E telling me to buy something new. But I wouldn't even know what to buy! LOL. I'm a big mess. I have such horrible fashion sense.... I'm hoping you guys have better fashion sense than me!