Match a slim fit wool pencil skirt with a chunky Fairisle knit, ankle boots give the whole look a fashion edge but try loafers for something altogether more preppy. The Chic Cream Tailored One ...

"For example, wearing a pencil skirt with ankle boots is tricky. You need to know how to style the top and play with proportions," says Appelt. If it gets colder, you can add tights since ankle ...

The pencil skirt is back in a big way this season, via Prada, Gucci, Fendi, Erdem and Calvin Klein. ... For an added relaxed appeal, team with a pair of black heeled ankle boots. 4.

Fitted Pencil Skirts + Slit Booties. Wearing a fitted skirt with any kind of boots has the potential to look awkward, ... Zara High Heel Ankle Boots with V-Cut Upper, $60; zara.com.

There's one thing I don't wear in cold-weather months: skirts. Wool pants, leather leggings, jeans—I stick to anything that (a) doesn't require tights and (b) can easily be worn with ankle boots ...

If you're on the hunt for the perfect fall shoes, look no further than ankle booties. As far as year-round footwear goes, they certainly take the cake. Wear them with shorts in the summer, tights ...