Quick answer - I'm lazy and don't feel like taking time to figure out my clothes (and yes that is what I told her, well I substituted busy in the mornings for lazy)
Long answer - I should but here's what's stopping me. Nice pants mean...
Nice shoes - I prefer sneakers as I don't have very many comfortable non sneakers
Thongs - aka butt floss. If you can find me a pair of nice pants I can wear without getting VPL, I'll buy 10 pairs
Taking time to plan - I do dress better on the days after I run because I have time to think about what I'm wearing, instead of dressing like a college guy and grabbing what's clean just to get out the door. My kids pick out their clothes the night before, I need to start doing this too.
Also I live under the delusion that if I am dressing in not so nice clothes I am more likely to clean my house. If I'm wearing nice pants I'm not getting down on my hands and knees to scrub the floor. I say delusion as there are many days that I dress in clothes I could clean in and then don't.
I know I've said this before but since my birthday is coming up, here's the plan. Get myself some comfortable but cute everyday shoes - I'm thinking ballet flats. Colored jeans seem like a good compromise on the pants and seem to be in style right now. Anyone have any good recommendations? They both certainly fit the comfort quotient, and as I admitted last spring, yes I do feel better about myself when I dress well, so time to get rid of what doesn't work and get stuff that does, and wear more of all the great Lia Sophia jewelry I've bought in the last year or so.
I've still got a few weeks until my birthday but am planning on taking a day off November 3rd and finally get my haircut after almost 2 years. I also think the haircut will help me try a little harder. Right now my hair is longer than it has been since college, so I put it in a ponytail or bun almost all the time. I'm thinking if I actually have to take a few minutes to style my hair in the morning, I'll be more likely to dress nicely.