It depends a lot on the dress, on the kind of hose you'll wear (if any) and the shape of your own legs (and your feelings about that.) The length/ shape of the dress or skirt is also relevant.
Obviously a more casual bootie would look better with a casual dress.
More refined (pointed toe, narrow heel, or some special leather) will look more dressy.
In my case -- my calves are proportionately short (and I am not tall) so one trick I've learned is keeping the contrast low. So...if wearing bare skin or nude hose, booties in a "nude for me" tone or one that blends pretty well with my skin tone will be leg lengthening. It doesn't have to be exact, but a taupe, cream, or pewter tends to tie in and extend the leg line with bare looking legs more than a dark bootie. If wearing hose, which I pretty much have to do for half the year, I try to tone it to the bootie. This means I'm restricted to dark footwear in winter quite a lot. Sigh.
Bookending your booties to your hair or some other outfit element is also useful. It might not extend the leg line but it gives the outfit cohesion.
The first pictured booties have a sort of V at the vamp. This is flattering since it extends the leg line like a lower vamp shoe. The style is from a few years ago and is not super current now, but still in style. It works especially well for dresses.
I've worn booties similar to the ones below (or the exact ones) with different types of skirts and dresses, with varying degrees of success. If the bootie has a higher shaft it is important for the fit to be fairly close if possible.
