$150,000 Done Right, Failing at Dressing for the Workplace

Recently I was asked to attempt to dress more professionally at work. I've no real issue with this (besides the expense) but I do suffer from a lack of stylistic direction. How does a 26 year old dress without looking too young, too old or not professional? My job also entails working with mostly older people in their 50s to 90s so being too trendy and flashy is an issue. I'll admit I'd been dressing like Pam from the Office, a variety of button up shirts and pants with flats.
I went out and purchased some skirts, my mom sent me a nice dress and I recently purchased several pairs of heeled winter shoes. I've even made an effort to wear pantyhose.
I really think dressing for success should be some sort of college class. Changing from the collegiate uniform of tee shirts and jeans to a professional "bank president" look (the image my boss gave me to aspire towards) has been very difficult for me. I've gained some weight while working my desk job and admittedly feel rather uncomfortable in my new, larger skin, and have an even harder time dressing myself. This is particularly rankling as I view myself as rather fashionable.
Take today for example. I am wearing a cute pair of red heeled ankle boots, houndstooth tights, a gray knee length pencil skirt, a gray blouse, a wide belt and a chunky red necklace. One of my patients came in and said "You look like you are getting ready to go out partying" (unprompted, I certainly did not ask him what he thought of my ensemble). Hurmph. And here I thought this outfit was one of my most professional yet. I'm still undecided about this outfit, I feel pretty in it, so would rather not decide it's a failure.
So here's the rub. Despite my disgust at Sarah Palin's views on many issues I really like the style she is being dressed in for her campaign (A style that's apparently cost GOP doners over $150,000 in the last two months). As opposed to Hillary, whose mannish suits seemed an attempt to disguise her femininity and negate any sex-appeal, Gov. Palin's outfits look professional, kicky and flaunt her womanhood without being overtly sexy. I do not think a woman has to dress like a man to be successful. Hillary did not need to pantsuit it up in order to be perceived as a competitor. Denying our lady hood is not feminist.

So, in taking a page from Sarah Palin's fashion book, would these knee high boots (I own a similar pair) be appropriate at work?


Has she broken the knee high boot barrier, allowing all of us (even those of us who work with the olds) to enjoy snug warm wintertime legs?

*Note, I just talked to my boss who said my outfit is probably OK, but knee high boots are only appropriate for hookers. alas.