I am new and still learning as well. As far as I can see, other than the sleeves length, you need to hem those pants. Also, first rule is that you NEVER button the bottom button for a two-button jacket. As for the cost, I believe it should be around $30 to shorten at both sleeves. I used to think that Black suit+Black shirt = SUPER COOL, but now I think that the only suit that work with black shirt is silver or grey, period. I think AE Strand is a great shoes. If possible, get the AE Strand. Not only that it looks cool, but it will last you a long time. However, if you will not going to get them this time, just go for black shoes. Do not wear square toe shoes.