Hi all, Before we begin, I just want to say I don't have much of a fashion sense. I shop at American Eagle and wear mostly simple stuff. I don't have much of an income to shop at more expensive places and still have plenty of school loans and other debt to pay off. I'm content with what I wear. Boot cut jeans (I'm not into skinny or relaxed jeans at all. I don't like the feeling. But that could change...), solid color shirts, I own a few button ups but not fancy ones, etc. I'm an extremely casual dresser, NOT preppy. I rarely wear polo's and no, I do not pop the collar . I've never owned or worn a blazer so this whole blazer thing is really new to me and adds that much more confusion. Now to get to why I'm here... I've done some bits of Google'ing and asking around in stores and it appears that I am getting mixed responses. I recently purchased my first basic blazer here: http://www.ae.com/web/browse/product.jsp?productId=2101_9424_410&catId=cat380145 Pretty basic from what I've read. I understand basic things like contrast. You don't want to wear similar colors. You want to have contrast to make things pop/stand out. I'd like to wear that blazer casually with jeans. Not dressy casually. I'm not the kind of person to wear dress pants/slacks/trousers/khakis/whatever-you-want-to-call-them often. I'm more comfortable in jeans. From what I've been told, I could go with a darker wash boot cut jean and look casual. If I tighten up to say a relaxed or straight jean, it would make things more dressy. But from what I'm reading on Google, you want to wear a lighter colored jean to have contrast. Which is it? Personally, I really don't like solid color jeans. I like them with some fade, whether they be light or dark. And then we have shoes... Oh God... I currently have one pair of shoes lol. These: http://cdn3.skechers-usa.com/img/productimages/xlarge/61181_WBK.jpg . Try not to hate . Like I said, I don't have much of a fashion sense and I'm really not too into fashion so I try to keep things basic. I could wear those shoes with the blazer, no? I'm thinking about picking up a black pair with a similar design so I can at least have 2 opposite colored shoes to be able to do different outfits and at least look somewhat matching. Sorry for the long read. I know I need a lot of help. It would really help if I had a girl/guy friend that knew all of this but everyone I know really doesn't do much with fashion other than business casual.