Help me! I insisted upon wearing a tie but had little time to think things through...
Emphasis on "little time".
Those shoes are a bit clunky, and they could use some TLC. The color isn't quite right for the suit. You set an otherwise high standard with this rig, in terms of both style and quality. The shoes don't live up to it. Also, though your tie and square are both nice, I wish they had a color in common to tie them together.
Parterre, that shirt is too formal to wear with anything less than a suit. I wouldn't really like it even then, but it wouldn't be so out of place. If you'd like to wear a tie, wear a coat, and be more afraid of stripes-on-stripes. Thin sweaters like that work better as layering pieces. Wear argyle socks, or even a colorful pair.
Right now, it looks like you're trying very hard to dress elegantly. If you directed that effort into a slightly different direction, you could do very well. Figure out what an appropriate level of formality is, and dress for that.
CottonDockers: Challenging oneself is well and good, but are you trying to dress well, or learn to be a better dresser? Athletes push themselves in training so that they don't have to push themselves as hard at the real thing, if you get what I'm putting out.
I was told to leave this package here...
Alright, I took a bunch of your advice yesterday and looked through a bunch of posts and decided to try something a little more traditional.
Light blue shirt, navy blazer, wool blend tie, gray khaki's, and boots cause it was snowing in the morning!
Watch is a Hamilton Khaki Automatic. Graduation gift from my folks.
(/me crosses fingers)