But with such a bold silhouette, figuring out how to wear cowboy boots can feel intimidating. Should you tuck your jeans in or let them stack? Do they work with dresses? Can you wear them outside ...

Stein recommends pairing your denim shorts with cowboy boots for a foolproof ... for a contemporary silhouette. Bring on the denim, fringe, and cowboy hats. Wearing flannel to a country concert ...