If you work at an enviroment where you are free to dress what you want but under the category of business or business casual, this look is easy to pull. I say this with confident because, im 5'0 and i look good in something like this. Confident is always a plus. Now for make up, i would use the shade of gray. And then later on after work you can always darken it.
After the long hours at work; most people including my self, change into something more comfortable. Comfortable does not mean pj's, you can look cute and comfortable at the same time. Most office business hours are 9 -5, this means you still have the time to go out to the mall or casual dinner out with your friends. This look is definetely shouts DOWN TO EARTH.