Lessons:

I really like trouser jeans in a dark wash that I could wear to work.

I have been wearing my jeans too short. WAY too short.

Boot-cut bores me now; I want a wider leg.

If I had had limitless funds this morning, I would have bought:
J. Crew Trouser Jeans (dark wash) $98
Gap Essential Jeans (dark wash, trouser-ish) $69.50
Gap Long and Lean Jeans (lighter more weathered wash, weekend jeans) $59.50

As it is I bought none, but am thinking about the Gap Essentials.

Pictures of my ass, with commentary, start here: http://www.flickr.com/photos/casperflea/2302303377/