How about in a casual setting?
Would you rather see her dressed more classy/put together (skinny jeans, flats, nice sweaters, tees, statement necklaces ) or more fun and girly? (dresses, shorts, bright colors)
Most Helpful Guy
For the workplace, I think it depends on what your agenda is for the day and of course who you want to impress.
If you're meeting clients, maybe the more professional look would work, gives them the vibe that you know your stuff. If you're in the office all day, probably something more comfortable but still look dependable to your bosses, wouldn't want them to think otherwise. If you're trying to impress your co-worker so that he asks you out, don't wait around and just ask him out. :D
In a casual setting, just dress how you want, I mean, c'mon! It's casual!
Also, for the makeup, just don't overdo it, I can't speak for all the guys on here, but too much make up just doesn't work for me.