Riestrella, I like the skinny jeans-tank top combo as well and think it always looks effortless and still chic.
I got to goal and within 12 lbs of my ultimate goal, was in a size 6 US or size 10 UK and still wore the exact same kinds of clothes I wore a 100 lbs heavier. I think I wore more fitted dresses but I still had the same hang ups about showing my arms and wearing sleeveless clothes etc. Go figure!
That said, this thread has made me think and I think my goal outfit would probably involve a pencil skirt with a button down or some other top tucked in, a slim belt and some killer high heeled pumps such as below: