It was in the mid-00s when booties came back. My first pair were Chloe, a major splurge from Bergdorf Goodman that kickstarted a love affair with the style that continues to this day.

Madewell’s Billie Boot is one of my top choices for the season, and I like everything about them: the color, the heel height, the profile, the price. Pair with a sweater and skinnies and a sweater dress and tights.