i've done short pants with boots. i think it mostly depends on what pants and what boots and how they work together and the look you're trying to go for. it's hard to say in the abstract. on top i'd suggest either a plain complementary bright solid. since it sounds like you're already rocking a lot of browns and earth tones you might try for an actual color like a pale blue? or something in the same color family as cream or coral? also, matching it with a cute tailored blazer or jacket i think really cleans things up, hides unwanted lumps, and such. i use these ALL the time.
and on the topic of things going in and out of fashion...watch out ladies: the hammer pants look appears to be making a comeback. god knows why. and women during fashion week in paris were spotted with pleated (PLEATED!) slacks finished with a french cuff at the bottom, which in my mind is more or less an upscale low-level hammer pant in and of itself. terrifying!!
