It's all about owning who you are. Some guys totally rock the converse with the rest of their nerdy intellectual look and it just pulls everything together, but that's also because of who they are. Not even Cinderella is going to care about what shoes you're wearing if you're charming and you make her laugh and she has fun being around you. Your personality is so much more than your choice in wardrobe. :)
where waht makes you comfy don't get to where your not being yourself and then you ll be even more shy and plus uncomfortable as long as your clean and not looking trashy you'll be fine. just have to be comfortable in your own skin that's going to be the most inviting and confidance goes quite a bit further so its worth bieng your confidant and comfortable :) with self!
Shoes matter as much as any other item of clothing in that they're part of the outfit. And you shouldn't wear an outfit for girls, you should wear it for you, dress as you like it, not as you think girls will like it. Wearing it for you creates a confidence in your appearance that most girls find attractive regardless of the actual clothing.