It's always been a staple in most women's wardrobe. It think, but I am not sure ... the Coco Chanel may have invented this look ... with her first Chanel suits.
In the 50's it was called the straight skirt (the "pencil" name is much more recent). It always reminded me of what a "secretary" would wear back then ... and with what they called "sweater girls", too. So ... I always think of pencil skirts as classic office wear but with some sex appeal. In fact, in the 60's, Mary Tyler Moore made a sensation wearing a pencil skirt on the Dick Van **** show. You could actually see the curve of her buttocks, which was considered very daring for TV at that time.
And nowadays, it still can be office attire or club attire, depending on what you top it with. I wear pencil skirts to dinner, to parties that are neither extremely dressy or casual, when I meet clients .... anywhere I want to look a bit dressy, but not overdone. The pencil skirt is probably the most versatile thing I have in my wardrobe ... I have several in different colors.
I"m a middle aged woman who is a stylist (just catalogs and stuff, basic clothes, not high fashion) but I used to work selling real estate, and before that I was a bank manager. I've used it in all three professions. I have an active social life here in L.A. and travel a lot ... so the pencil skirt is still my friend. It's ageless ... which I like. It can look good on a woman of any age.
I actually don't prefer one brand of pencil skirt over another ... the are so simple and so classic, that it really doesn't matter to me. It's how you accessorize it that makes the difference.