For the most part, I have always kept away from the "matchy-matchy" look -- it's just not my personal style. However, I've been warming up to that approach, and am really loving the look of matching patterns, especially skirts/pants + shoes. It achieves such a fresh look without trying too hard, and is best if the top is kept simple and classic.
(PS sorry for the J. Crew overload, they are killing it with their patterns right now).
STRIPES
1. J. Crew skirt $128
1. J. Crew skirt $128
2. American Eagle flats $29
ANCHORS
3. J. Crew skirt $98
4. J. Crew pumps $228
POLKA DOTS
5. AG jeans $178
6. Madewell flats $98