Hi, 50! I think body shape really has more to do with it than size. When you try on the skirt you are probably more focused on what you think is your worst feature. But we have to look at the big picture.
Would you be able to try one and take a photo?
I'm very curvy and a pencil skirt is the only way to go. Length is also very important.

Somepencil skirts narrow toward the bottom, and some are more straight and go straight down from the hip. Of course, your body shape will influence how the skirt falls as well. If you have heavier thighs, try a stright cut pencil skirt that does not narrow. You shouldn't have to size up for a pencil skirt- they are cut to fit close to the body. I hvae seen denim pencil skirts at Old Navy and Kohl's, banana republic and Ann Taylor. Have you actually tried any on yet? You might be surprised. They really are not just for the model thin girls. I am currently sporting a size 14 denim pencil skirt, and I am loving it.

Great advice from Sarah and Khris.

Pencil skirts do not need to taper at the hem. If you're bottom heavy, you need a pencil skirt that falls straight from the hips down. That will flatten the curve. Its when you want to accentuate the curve that you taper in at the hem.

I have clients from size 0 to 22W in pencil skirts. It’s a great look if you get the shape AND length right.

Pencil skirts, to me, are particularly gorgeous on curvy women of ALL sizes (and great for giving the illusion to less curvy women as well)! I'm about a 12/14, and I definitely understand how frustrating it is to find the right type of pencil skirt. I managed to find two in the past few months that fit well, one from Ann Taylor that has more of a straight cut and one from Macy's (Calvin Klein brand) that tapers a bit. In addition to what Sarah, Khris, and Angie have told you, I'd suggest trying a skirt with just a little stretch to it. It should help with that tight fit feeling, especially through the hip and thigh.

Thanks...I am willing to try if I can find the one that hangs straight down and doesn't taper that is avail. in a size 16...any links you can refer me to? I so much appreciate this wonderful community who are so helpful!

I find that you need a longer skirt if it tapers slightly. I have this one, and love it to pieces:
http://www.anntaylor.com/catal.....pe=Regular

Maybe this visual will help. Here's a straighter pencil:
http://www.anntaylor.com/catal.....pe=Regular

And here's a severely tapered pencil:
http://www.anntaylor.com/catal.....pe=Regular

Fabric has a lot to do with it too. Maybe you could make a trip over to Ann Taylor and try on the various pencil skirt styles to see which one/s you like best?

These are at JCrew in your size:
http://www.jcrew.com/AST/Brows...../19326.jsp
http://www.jcrew.com/AST/Brows...../17607.jsp
http://www.jcrew.com/AST/Brows...../91380.jsp

Banana Republic:
http://bananarepublic.gap.com/.....pid=685380
http://bananarepublic.gap.com/.....pid=674695
http://bananarepublic.gap.com/.....pid=670881

Let me know what you think of these and if you want more links. These look straighter to me in the photos, but as always you'll only know if you try them on.

I have to agree that, in my opinion, a pencil skirt actually looks better if you have some curves. I have a rectangular figure, with a bit of a belly, and look silly in a pencil skirt, but I bet you'd wear one well if you find the right fit.

Like finding the perfect pair of jeans, you may have to try on 50 before you get the right one, but when you do, it will be well worth the effort.

It can be challenging to find a pencil skirt that fits well if you have wide hips, though I think pencil skirts look good on curvy women. I recently bought a pencil skirt, but to get a size that fit my hips without looking vulgar I had to go up so many sizes at the waist that the alterations are going to be very expensive. The skirt looked much nicer once the tailor had pinned it, and I'm hoping the investment in fit will be worthwhile. However, the tailor warned me that she probably wouldn't be able to get the waist small enough, even though she was already taking it in in three spots, and, at that, she suggested I go up another size in the hips the next time. It's frustrating that pencil skirts are frequently recommended as flattering for hourglass women but not really cut to fit them.