Fall is filled with earthy hues so embracing a utilitarian vibe feels like a natural progression.  Classic elements with a military meets equestrian attitude have wardrobe staying power, but often carry with them more masculine connotations; which is why it took me until recently to realize the value of having an army green canvas jacket in my arsenal.  When combined with knee-high riding boots, suddenly delicate elements like a ladylike dress and mini box clutch become chicly rugged.

{J. Crew dress (found at a sample sale in NYC ages ago); Timberland boots (similar); Talbots jacket (similar); Ray Ban sunglasses; vintage clutch, bracelet, and earrings}