I think it works! Then again, I'm no expert, so you may not want to trust my judgment on it. I know for me, wearing khakis can entirely throw me off. I'm not really a khaki type person and just feel all kinds of strange wearing them, even though it makes no sense because they're just pants. You're probably not as strange about them as I am. ;) Maybe try a bright pair of shoes or throw in a bright necklace or scarf?

I think the layered tops/jacket are super cute, and the pants fit well, but the proportions are off. A longer shirt (just slightly) would work better with those pants. I would also pair the top with a slightly less contrasting bottom.

I would agree with navillustrious on both points. I have a similiar looking bottom half to you Kendra, and I have really taken to wearing tops at Angie's perfect top length for pants.
http://youlookfab.com/2008/04/.....and-pants/

Thanks guys!
I agree, the khaki's might not throw me off as much with a lighter colored top under the jacket.
But when I first got dressed I put the navy top on with jeans and felt the whole thing was too dark... how to I reconcile that? The top is too dark to match with khakis, but when put with jeans makes everything too dark... ugh

I don't care for khaki's. Can you try a twead or micro check for pants?

I think the pants fit you really well and are quite flattering, and I do think the black does work really nicely with your hair color.

Perhaps you just need to accessorize the outfit to take it from ho-hum to fab?

I like the blue top underneath, another idea is to bring in red, like a red tote bag. And the shoes - an animal print on the shoes would be killer. Red or yellow or even orange shoes would also work.

A touch of cream or white somewhere (bag, watch, necklace?) would also help. I do really like the combo of khaki (or taupe or camel) with black and white. Hmm... how about a black and white checked scarf or hat?

So basically, instead of blue, bring in white/cream or red, and see how that works.

A jean jacket also looks adorable over a black top with khakis. Add converses or dock shoes in a bright color and there you go!

WOW, amazing ideas Shiny! Thanks so much!

I will definitely be trying some.