"You just don't wear an ordinary skirt or dress with cowboy boots unless you are wearing your cowboy boots to milk the cow...If you square dance or line dance there are special outfits to wear with your cowboy boots. The square dance outfit is a ruffled and tiered square dance skirt with a peasant type blouse or western style blouse."
As I don't own any long suede skirts or fringed jackets, I might follow advice from eHow.com instead:
1) Invest in a good quality pair of cowboy boots, since you will likely have these for a long time. Look for a neutral color, such as black, brown or camel.
2) Consider opting for special details such as contrast stitching or hand tooling.
3) Wear cowboy boots with jeans and a long cardigan or tunic. This look can go just about anywhere you do on the weekends or after work.
4) Slip cowboy boots on over skinny jeans and a dress. This is a look some of the celebrities have been seen in lately and is a very clean, modern style. Realize that the skinny jeans can look almost like tights if they are fitted enough.
5) Try cowboy boots with a cocktail dress and dark tights to add a casual and unexpected vibe.
6) Step into cowboy boots beneath nicer wide leg pants. The narrow point of the toe will give you a long, sleek line.
7) Consider wearing cowboy boots with a mini skirt and layer tanks. This is a sexy, confident style for a night on the town that won’t look like you are trying too hard.
8) Remember that you don’t have to dress like a cowgirl to wear cowboy boots. These can be a nice addition to modern, conservative and trendy pieces.
Another website strongly recommended not going "cowboy themed." Unless you want to end up looking like Daisy Dukes, that seems like sound advice to me.
Image lifted from zappos.com