Fair question. It's a slow process I think. A couple things I've learned recently (from SF no less) is that I owned a lot of poor fitting, average quality items. At the end of the day, the way I've always dressed is casual and a street wear look outside of work. I used to suit up daily and didn't think much of weekend wear, but I have not worn a suit to work for about 2 years now and I never updated my wardrobe to suit.
So this first step has really been about adding color, increasing the quality and feeling comfortable while doing so. The reality is, I work in a very casual environment, and while these items may be quite commonplace on this forum, in my world they're miles ahead. The look and style I admire is too formal for my office and I have only just started to introduce tucked shirts / blazers into my fits for more formal days (client meetings etc).
Some risks can certainly be taken from here. Let's see what 2013 brings.
Here's a few examples of a more formal look vs casual look in my current wardrobe.