Remember that feeling? The first day of school, slipping your feet into a fresh-out-the-box pair of penny loafers—no one could tell you anything. And, apparently no one can tell fashionista Chloë Sevigny anything either. The actress known for her roles in American Psycho (2000, Lions Gate) and HBO's Big Love has funneled inspiration from her Connecticut roots to resurrect a classic. Partnering with Opening Ceremony and Bass, Chloë journeyed down a nostalgic path to create a collection that offers something timeless—and the loafers ($160-$170) make the biggest statement. From the well-stitched seams to the striking color combinations to the supple leather panels, these are must-have flats.

Those who seek to complete their fall look with sophistication need these in their closet. And though these loafers have no slot for a penny, they do offer a crisp, clean look that make your feet look like a million bucks.

Shirea L. Carroll is a journalist and online TV host based in New Jersey. Follow her on Twitter.