It depends on the style of the dress.

This is really cute, and would look fantastic with black thigh/knee-high heel boots. It's only $39.99 at Target.com.


This one would look better with a pretty set of heels though. (Only $29.99 at Target.com.)


If you're willing to spend a little more, check out Bluefly.com. They've got designer dresses for less (not all of them are cheap but if you take the time to look through every page of dresses or whatever, you'll find something reasonable).

Basically, if you've got a classy or Sunday looking dress going on, boots aren't the shoes to wear. If it's a cute, funky dress or skirt though, it can work.