I can't decide whether I think this worked. Seems like too many right angles. I originally thought to wear a solid grey wool tie, but it was too close in color to the pants. I also considered switching the colors of the tie and square, but a brown tie seemed too matchy. Suggestions appreciated.
Plaid on plaid is pretty much always bad.
Knits. Emblematics. Repps. Big paisleys. Not plaids or neats. Wool solids would be okay, but gray is a bit boring.
Also, is that a gray shirt? That would be an issue.