I know your sweatshirts and pencil skirts don't mingle much, but maybe they should. At least that's what I'm thinking since Rachel Roy's ladylike goes cool combo caught my eye. While your pencil skirt lends femme sophistication, your slouchy sweatshirt top is totally effortless; when they meet, it's dressed-down chic at its best. Don't complicate things, feel free to play with textures and prints, just avoid bulky sweatshirts with too much length or width — extra cool points if you opt for a leather pencil.
I know your sweatshirts and pencil skirts don't mingle much, but maybe they should.