With my first pregnancy, at first I was in shock of how I looked. I was the type girl growing up and in college that whenever I tried clothes on, I would always ask myself or friends if "it made me look pregnant". So I had a little bit of a hang-up about looking that way going into pregnancy.
At first I really tried to hide it and not even look at myself, which was hard by the way since I was teaching dance full time and in front of a mirror 4 days a week. But at about 6.5 months I realized that I didn't look "bad" or "weird", that it was normal.
Fortunately, I am 5'10" with a slender build, so I only looked pregnant from the side. If you looked at me straight on or from the back, you couldn't tell. From then on I would wear more things to show off my bump. I embraced it the rest of the pregnancy with cute clothes and dance wear.
With my 2nd pregnancy, I was on bed rest for the final 5 months, so nobody saw me anyway, and I usually wore sweats or pi's all day. :( It wasn't near as fun.