North of the Manhattan madness, you’ll find a quiet haven of old money living, which includes sprawling family estates, acres of rolling land and country clubs in every town. Equal parts timeless, rustic and luxe, upstate New York fashion is just as swoon-worthy as the aesthetic, and I found 17 stylish fall pieces that could be straight out of a Tuxedo Park boutique. Classy wool sweaters, Chelsea boots, straight-leg jeans and tailored-looking dresses are just a few staples in every upstate rich mom’s wardrobe, and these styles get you the look. Whether you’re running errands, apple picking or...