Riding-inspired chic meets downtown cool with the help of a few key pieces. As the temperatures dip, layer a cinched wool jacket over a curve-hugging sweater dress and finish off with tall boots to create the ultimate in cozy, contemporary allure.

1 Mike & Chris Ethan Jacket w/ Belt Mike and Chris is famous for its luxe leather outerwear, but crafts wool outerwear with equal aplomb. The skinny belt yields a feminine shape and an earthy contrast of colors.

2Left on Houston Liberty Sweater DressWe love the colorblocked hues on this sweater dress, covering all of the neutral bases.

3Frye Paige Cuff BootsThese great equestrian-style boots really pull this ensemble together, with the coppery brown buckles coordinating with the dress and the jacket’s belt in a way that feels effortless and not too matchy-matchy.