#1738: Always check the weather forecast before breaking in new shoes, especially if you're attending an event where you'll be standing for two and a half hours.
It wasn't the standing, in and of itself. It was the fact that when I walked to the T it was merely cold outside, and when I exited the underground station downtown, there was a full-on snowstorm, icy brick streets and all. It took me 10 minutes to stagger 5 blocks to the event, and it was worse two and a half hours later.
Unfortunately, heels don't double up as ice picks. I tried.
#1739: There is no such thing as overdressing.
I also had my Northwesterner complex about underdressing, so I decked out in what I thought was overdressing for a friggin' rally. (A rally, people! Local politicians get up, tell you why they endorse so-and-so, there's usually some child who's trotted out, and then the candidate gets up and guilt-trips you into signing up to canvass in New Hampshire before the primary, which you will try to get out of by volunteering to phonebank instead. Very different from a fundraiser, where you look snazzy to convince fellow donors you're important.) At home, the elected officials themselves frequently speak in public in jeans and a T-shirt. This time, I was Banana Republic head to toe, except for the shoes.
Turns out, I was dressed entirely appropriately, but underaccessorized (not to mention bedraggled, with snow-wet hair), and thus still under-attired.