Dressing very casually for a date

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ok, I have a confession. I've just remembered that the last time I saw the man I like he was wearing a polo shirt. I did think it was dorky at first, but completely forgot about it because I enjoyed his company.

Wear whatever you like. It doesn't matter.

Okay, I’ll dress up a bit.

I have a bunch of long-sleeve button-down shirts (plaid and solid-color). I have a pair of black nike sneakers (nike air pegasus) and a pair of black adidas sneakers (adidas gazelle). If I wear a pair of relaxed fit (not baggy, but not slim-fit) jeans, a black long-sleeve button-down shirt and a pair of sneakers, would that be okay? Does that outfit sound like a good plan? Can those sneakers still go well with jeans and a long-sleeve button-down shirt? Or would sneakers ruin that look? I’d really rather avoid wearing dress shoes because I have knee problems and wearing dress shoes aggravates it, especially if I walk for extended periods of time, and they also tend to cause blisters.

In general, do the sneakers I described go well with jeans and a long-sleeve button-down shirt? And in general, do long-sleeve button-down shirts go well with jeans (even if you’re wearing dress shoes)? I want to look like I put some effort into my appearance while still being able to walk comfortably (part of the reason I dress so casually is because of comfort).

Here are pictures of the sneakers that I have:

http://www.prodirectrunning.com/product ... /71947.jpg
http://www.zappos.com/images/z/3/5/5/1/ ... 3-p-4x.jpg

Here are pictures of the type of fit for the jeans that I have (I have the same color):

http://fashion.tractshop.com/wp-content ... 4x34-0.jpg

Yes your outfit plan sounds good.

Depends on the dress shirt though. A white one or a pale blue one that you would wear with a suit would look mismatched with jeans, but I think a black one with jeans and your black sneakers will look good. A plaid shirt would look good too.

Honestly this doesn't sound too casual at all. No need for dress shoes.

Good thing you're not a woman, our dress shoes would kill your knees.