L'Oreal Wear Infinite Single Eye Shadow, Plum Roya

There have been endless style incarnations of this 50s-inspired style icon--this Joie leather jacket taps into your rebellious side while steeped in elegant and decidedly feminine details.

Western inspiration comes to life in a luxuriously soft suede skirt, crafted with a straight-wrap silhouette with fun fringe trim.

Putting a modern spin on timeless tweed, this Donna Karan New York tunic, with a cowl neck that drapes ever so slightly off the shoulder, can be worn solo or over leggings and tights as the weather cools. Work or weekend, it's ever so cool belted with knee-high boots.

Step out in style, gray skies notwithstanding, in these elegant, equestrian-influenced Ralph Lauren Collection rain boots.