Given that they're a practical necessity, I've tried to get past how I look in them. That said, I prefer shorts with a longer inseam (8 inches seems to be my ideal). I don't worry about the tan line. For one, it's a badge of honor and, for another, I don't wear much (at least in public) that doesn't hide it.
Plus, I've found that some shorts make my butt look bigger than others. I've become a huge fan (thanks to Susan at TE's suggestion) of the Sugoi RS short because the material provides quite a bit of compression and the chamois stops short of padding my entire booty. I have also found that you kind of get what you pay for when it comes to shorts. The higher end models not only have better chamois pads, but the material itself seems to "lock and load" a bit better.
Live with intention. Walk to the edge. Listen hard. Practice wellness. Play with abandon. Laugh. Choose with no regret. Continue to learn. Appreciate your friends. Do what you love. Live as if this is all there is.
--Mary Anne Radmacher