Sorry for the lack of updates, life's been busy.
It's become sort of a routine. A few times a week when I go to work, I stop by a mall, switch into some heeled shoes and go in. Usually grab something at a coffee shop and sit in the food court and work for an hour. Sometimes I do some shopping/browsing. Usually am able to spend an hour doing this. Getting out of the car is not an issue 90% of the time anymore. I didn't expect those 4.5" stiletto boots I bought for USD$15 to change everything. They fit perfectly, and go with my casual-suit perfectly. They've become my go-to shoes, and have spent a lot of time in them already. I've gone back to the store I bought them from, hoping they would have another pair, but they didn't (had to ask the sales lady - and was wearing those same shoes while doing so!). Anyway, I attribute a lot of my progress to that pair of heels.
Have also worn pumps a few times, and a few other pairs of boots. Usually with dress-pants, but sometimes with long jeans. Want to wear more pumps... Have worn skirts (without heels) a few times, trying to keep it professional looking, but they're super comfortable. Once in a rare while I am able to do skirts with heels, that's fun!
One of my most recent purchases is a pair that looks like this:
I just find those to be awesome in shape, colour, everything. And, to me, they look quite manly under dress-pants.
Anyway, lots of progress I think...
[why are my images squished??]