@kml, thanks. While my son was at a playdate, I went shopping. I ultimately decided not to buy "flashy" clothes. I closed a $4M deal this week and speak in front of 100-200 people. That's not because I'm Mr. Fancypants. It's because I'm personable and approachable. I've met many C-level execs--like you, it's rare an occasion requires fancy dress. I'm not big on galas. The places where Ms. Sunshine felt I should have dressed fancier, I was already among the top-dressed. I think she wanted me to dress up more so she could dress up more without feeling out-of-place.
I did buy black dress pants for $40 (for work) and a solid maroon flannel for $30 (for the holidays). I also bought pre-threaded needles for $10 to repair two existing garments.