First off, I used to be a stylist for Nordstrom, Express, Banana Republic, Saks Fifth Avenue and Salvatore Ferragamo. Everything I suggest comes from experience. I keep up with current fashion trends and I have been to many fashion trade shows since one of my businesses is in the trade show display industry. I am very critical of myself first before giving anyone any fashion advice. Just my disclaimer
Your overall look isn't too bad. It is kind of plain and makes you blend in to the crowd. Designer jeans tells a girl you know your ish, especially if they are style conscious...which most of 8,9's and 10 are. (7forallmankind, Rock & Republic, Diesel, G-Star, True Religion). Jeans can also become a topic of conversation...almost like peacocking. Then when she brings it up, you down play it..
The Black Shirt is cool. To levelup: Look for a nice Grey vest. Check out John Varvatos @ Nordstrom.
Accessorize:
Try some silver chain-linked bracelet on the right wrist and a nice watch on the left wrist. Accessorize. Have something that can become noticeable and possibly a topic of conversation. Suggestions? If you have some money to spend check out David Yurman. Awesome & masculine looking jewelry. If you want to keep it conservative, check out your local jewelry shops at the Mall. I am sure you will find something you will like.
Shoes: Nice. Check out: Mark Nason Shoes
http://www.marknason.com
Great way to stand out - by default!!!