Most Helpful Girl
That all depends on what you're doing, what time it's at, and your sense of style. Here's what I go with:
Early dinner (like 5) or lunch, non formal - "natural look" makeup (foundation, touch of bronzer, discrete eye liner, mascara, eyebrows), nice jeans and a shirt that makes you look good.
Day out (piknik, day activities) - "natural look" makeup, your regular day outfit that you think you look best in.
Late evening dinner- dress or skirt, heels (if you can walk in them), nice flats if not. Make up should be complete, tasteful and a little stronger than the natural look (you can add eye shadow, darker eye liner, and lips). You mentioned dresses just aren't your thing, so I would go with nice jeans (or leggings) and a fancy top.