I was the same way for a long time and didn't think too much about my jeans. I realized, girls spend a ton of time not only looking for well fitting jeans for themselves but at other guys jeans.
When I made the switch to my Diesels from my Levis I found a complimenting set of washes (dark, light, and colored) and fits (straights and slim bootcuts). I've gotten more compliments on jeans from female coworkers then any other casual piece in my wardrobe.
Go for straight leg, dark wash pair of jeans first. Pros: You can wear them while going out and for casual office days with a jacket. Also straight legs compliment just about any body type. Hope this helps.