I started the lettering based on an elegant, yet modern typeface. I created both a slab serif and a more western type serif, both which add an Americana feel to the letters. The western slab serif version adds just a tinge of vintage while keeping the overall design contemporary. Altogether it has a simple and organic flow. I added some boot-like embroidery and arrow flourishes in a circle keeping with some of your brief suggestions, but I'm working on a stand-alone lettering as well for multiple brand design usage.